Supporting Information
|
|
|
- Henry Hall
- 5 years ago
- Views:
Transcription
1 Electronic upplementary Material (EI) for ChemComm. This journal is The Royal ociety of Chemistry upporting Information Controllably, C C Triple Bond as One-Carbon ynthon to Assembly of Benzothiazole Framework Yubing Huang, Donghao Yan, Xu Wang, Peiqi Zhou, Wanqing Wu,* and Huanfeng Jiang* Key Laboratory of Functional Molecular Engineering of Guangdong Province, chool of Chemistry and Chemical Engineering, outh China University of Technology, Guangzhou, P. R. China cewuwq@scut.edu.cn, jianghf@scut.edu.cn Contents A. General Methods... B. General Procedures... C. Optimization of the Reaction Conditions... D. Free Radical Verification Experiments... E. Deuterium-labeling Experiments... F. Characterization Data for Products... G. References... H. X-ray Diffraction Parameters and Data for d... I. MR pectra...
2 A. General Methods Melting points were determined with a Buchi Melting Point B- instrument. H and C MR spectra were recorded using a Bruker DRX- spectrometer with CDCl as solvent. The chemical shifts are referenced to signals at. and. ppm, respectively, and chloroform is solvent with TM as the internal standard. IR spectra were obtained either as potassium bromide pellets or as liquid films between two potassium bromide pellets with a Bruker TEOR spectrometer. Mass spectra were recorded on a Thermo cientific IQ gas chromatograph-mass spectrometer. The data of HRM was carried out on a high-resolution mass spectrometer (LCM- IT-TOF). TLC was performed by using commercially prepared - mesh silica gel plates and visualization was effected at nm. Unless otherwise noted, all reagents and solvents were obtained from commercial suppliers and used without further purification. B. General Procedures General procedure A: the synthesis of benzo[d]thiazole products au: In a test tube, a mixture of -iodoaniline (. mmol), (. mmol), phenylacetylene (. mmol), CuI (. mmol), K PO (. mmol) and,-phen (. mmol) was stirred in DMO (. ml). The reaction was allowed to stir at C under atm O for h. After that, water was added and extracted with ethyl acetate twice. The combined organic phase was dried over a O and concentrated. The residue was purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate (PE/EA = : :) as the eluent to afford the desired product. General procedure B: the synthesis of benzo[d]thiazole products a-p: In air, a ml chlenk tube was charged with -iodoaniline (. mmol), (. mmol), phenylacetylene (. mmol), CuTC (. mmol), DBU (. mmol) and. ml MeC/H O (:). The flask was evacuated and filled with nitrogen for three cycles. The reaction was allowed to stir at C for h. After that, water was added and extracted with ethyl acetate twice. The combined organic phase was dried over a O and concentrated. The residue was purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate (PE/EA = : :) as the eluent to afford the desired product. C. Optimization of the Reaction Conditions Table. Optimization of the Reaction Conditions a,b entry [Cu] base additive (equiv) solvent Yield d (%) CuI K CO - DMO n.d CuI K CO - dioxane trace n.d CuI K CO - IPA n.d n.d CuI K PO - DMO n.d CuI KOAc - DMO n.d a a
3 CuI K PO TBAI () DMO n.d CuI K PO,-phen (.) DMO () e n.d CuTC DBU MeC CuTC DBU MeC c trace CuTC DBU MeC/H O (:) n.d () e CuTC DBU MeC/H O (:) n.d CuTC DBU MeC/H O (:) n.d CuTC DBU H O n.d CuTC DBU,-phen (.) MeC/H O (:) n.d a Reaction conditions (entries -): a (. mmol), (. mmol), a (. mmol), CuI ( mol %), base ( equiv), additive in. ml solvent at C under atm of O for h unless otherwise noted. b Reaction conditions (entries -): a (. mmol), (. mmol), a (. mmol), CuTc ( mol %), DBU ( equiv) in. ml solvent at C under for h unless otherwise noted. c uper dry acetonitrile. d GC-M yield using n-dodecane as an internal standard. e Isolated yield. As indicated in Table, -Iodoaniline (. mmol), (. mmol) and phenylacetylene (. mmol) were chosen as initially investigated substrates. Through series of copper salts and alkali screening, we believed that the use of CuI and potassium is more conducive to the formation of -phenylbenzo[d]thiazole (a). When the reaction was performed in the presence of CuI ( mol %) and K CO ( equiv) using DMO as solvent at C under atm of O, - phenylbenzo[d]thiazole (a) was obtained in % yield (entry ). Other solvents including dioxane, IPA and MeC did not effect on improving the yield of a (entries ). When K CO was replaced by K PO or KOAc, % and % yields were obtain, respectively (entries -). In order to further improve the yield, different additives were tested in the system (entries -). The result showed that the addition of phase transfer reagent (TBAI) did not work in the reaction system, while the yield increased to % when using,-phenanthroline as a ligand (entry ). ext, when the reaction was performed in the presence of CuTC ( mol %) and DBU ( equiv) using. ml of MeC as solvent at C under, -benzylbenzo[d]thiazole (a) was delivered in % yield and % yield of product a was detected (entry ). The use of super dry acetonitrile was not conducive to the conversion, making the yield of a drop to % (entry ). ubsequently, we replaced MeC with a mixed solvent MeC/H O (:), and the desired product a was delivered in % yield (entry ) with no product a detected. When increasing the proportion of water in the mixed solvent, the yield was decreased slightly (entries -). However, the reaction could not proceed well when water was used as a solvent (entry ). Besides, when adding a ligand in the system, the yield was reduced to % (entry ). D. Free Radical Verification Experiments
4 cheme. Free radical verification experiments. Condition A: CuI ( mol %), K PO ( equiv),,-phen ( mol %), DMO, O, C, h. Condition B: CuTC ( mol %), DBU ( equiv), MeC/H O (:),, C, h. E. Deuterium-labeling Experiments cheme. Deuterium-labeling experiments. Reaction conditions: a (. mmol), (. mmol), a (. mmol), CuTC ( mol %), DBU ( equiv) in. ml MeC/D O (:) at C under for h unless otherwise noted. Isolated yield. The product d -a was determined by H MR.
5 F. Characterization Data for Products -Phenylbenzo[d]thiazole (a). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ): δ.-. (m, H),. (d, J =. Hz, H),.-. (m, H),.-. (m, H). C MR ( MHz, CDCl ): δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(p-tolyl)benzo[d]thiazole (b). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ): δ. (tt, J =.,. Hz, H),.-. (m, H),. (s, H). C MR ( MHz, CDCl ): δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Ethylphenyl)benzo[d]thiazole (c). Yellow solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ): δ. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),.-. (m, H),. (dd, J =.,. Hz, H),. (t, J =. Hz, H). C MR ( MHz, CDCl ): δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Methoxyphenyl)benzo[d]thiazole (d). White solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H O [M+H] + :., found:.. -(-Chlorophenyl)benzo[d]thiazole (e). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),.-. (m, H),. (t, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H Cl [M+H] + :., found:.. -(Benzo[d]thiazol-yl)benzonitrile (f). White solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (t, J =
6 . Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -([,'-Biphenyl]--yl)benzo[d]thiazole (g). Yellow solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (t, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(m-tolyl)benzo[d]thiazole (h). Yellow oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (s, H),.-. (m, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(Thiophen-yl)benzo[d]thiazole (i). White solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (t, J =. Hz, H),.-. (m, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(Pyridin-yl)benzo[d]thiazole (j). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),.-. (m, H). C MR ( MHz, CDCl, ppm) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(aphthalen-yl)benzo[d]thiazole (k). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),.-. (m, H),.-. (m, H),. (t, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:..
7 -Methyl-phenylbenzo[d]thiazole (l). Yellow solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ.-. (m, H),. (d, J =. Hz, H),. (s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Fluoro-phenylbenzo[d]thiazole (m). Yellow solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl, ppm) δ. (ddd, J =.,.,. Hz, H),. (dd, J =.,. Hz, H),.-. (m, H),.-. (m, H). C MR ( MHz, CDCl ) δ. (d, J =. Hz),. (d, J =. Hz),.,. (d, J =. Hz),.,.,.,.,. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz). IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H F [M+H] + :., found:.. -Bromo-phenylbenzo[d]thiazole (n). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ.-. (m, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H Br [M+H] + :., found:.. -Methoxy-phenylbenzo[d]thiazole (o). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ.-. (m, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H O [M+H] + :., found:.. -Phenyl--(trifluoromethyl)benzo[d]thiazole (p). Yellow solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (s, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),.-. (m, H). C MR ( MHz, CDCl ) δ.,. (d, J =. Hz),.,.,.,.,.,. (q, J =. Hz),. (q, J =. Hz),.,. (q, J =. Hz),. (q, J =. Hz). IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H F [M+H] + :., found:..
8 -Methyl-phenylbenzo[d]thiazole (q). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ.-. (m, H),. (s, H),. (d, J =. Hz, H),.-. (m, H),. (d, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Chloro-phenylbenzo[d]thiazole (r). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,,,. HRM (EI) (m/z): calcd for C H Cl [M+H] + :., found:.. Methyl -phenylbenzo[d]thiazole--carboxylate (s). White solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (s, H),.-. (m, H),. (d, J =. Hz, H),.-. (m, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H O [M+H] + :., found:..,-dichloro-phenylbenzo[d]thiazole (t). White solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ.-. (m, H),. (s, H),.-. (m, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H Cl [M+H] + :., found:.. -Chloro--fluoro-phenylbenzo[d]thiazole (u). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (s, H),. (d, J =. Hz, H),. (d, J =. Hz, H). C MR ( MHz, CDCl ) δ.,. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.,.,. (d, J =. Hz),.,.,. (d, J =. Hz),. (d, J =. Hz). IR (KBr, cm ):,,,,,,,,,. HRM (EI) (m/z): calcd for C H ClF [M+H] + :., found:..
9 -Benzylbenzo[d]thiazole (a). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (m, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Methylbenzyl)benzo[d]thiazole (b). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Fluorobenzyl)benzo[d]thiazole (c). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (ddd, J =.,.,. Hz, H),. (m, H),. (s, H). C MR ( MHz, CDCl ) δ.,. (d, J =. Hz),.,.,. (d, J =. Hz),. (d, J =. Hz),.,.,.,.,. (d, J =. Hz),.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H F [M+H] + :., found:.. -(-Bromobenzyl)benzo[d]thiazole (d). Yellow solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H Br [M+H] + :., found:..
10 -(-Methoxybenzyl)benzo[d]thiazole (e). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (m, H),. (m, H),. (s, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H O [M+H] + :., found:.. -(aphthalen-ylmethyl)benzo[d]thiazole (f). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (m, H),. (d, J =. Hz, H),. (m, H),. (t, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Hexylbenzo[d]thiazole (g). Yellow oil, Yield mg (%). H MR ( MHz, DMO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (t, J =. Hz, H),. (dd, J =.,. Hz, H),. (m, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H). C MR ( MHz, DMO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Heptylbenzo[d]thiazole (h). Yellow oil, yield mg (%). H MR ( MHz, DMO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (dd, J =.,. Hz, H),. (t, J =. Hz, H),. (dd, J =.,. Hz, H),. (m, H),. (t, J =. Hz, H). C MR ( MHz, DMO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:..
11 -Octylbenzo[d]thiazole (i). Yellow oil, yield mg (%). H MR ( MHz, DMO-d ) δ. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (t, J =. Hz, H),. (m, H),. (m, H),. (t, J =. Hz, H). C MR ( MHz, DMO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Cyclopentylethyl)benzo[d]thiazole (j). Yellow oil, yield mg (%). H MR ( MHz, DMO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),.-. (m, H),.. (m, H),.. (m, H),.. (m, H),.. (m, H),. (dd, J =.,. Hz, H). C MR ( MHz, DMO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(Hex--yn-yl)benzo[d]thiazole (k). Yellow oil, Yield mg (%). H MR ( MHz, DMO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (td, J =.,. Hz, H),. (dt, J =.,. Hz, H),. (dt, J =.,. Hz, H). C MR ( MHz, DMOd ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(-Phenylpropyl)benzo[d]thiazole (l). Brown oil, yield mg (%). H MR ( MHz, DMO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (t, J =. Hz, H),. (m, H),. (dd, J =.,. Hz, H). C MR ( MHz, DMO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm - ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:..
12 -(Pyridin-ylmethyl)benzo[d]thiazole (m). Yellow oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (m, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -(Thiophen-ylmethyl)benzo[d]thiazole (n). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Benzyl--methylbenzo[d]thiazole (o). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (s, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. -Benzyl--fluorobenzo[d]thiazole (p). Brown solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (dd, J =.,. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (m, H),. (dt, J =.,. Hz, H),. (s, H). C MR ( MHz, CDCl ) δ. (d, J =. Hz),. (d, J =. Hz),.,.,. (d, J =. Hz),.,.,.,. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.. IR (KBr, cm ):,,,,,,,,. HRM (EI) (m/z): calcd for C H F [M+H] + :., found:.. -Benzyl--(trifluoromethyl)benzo[d]thiazole (q). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (dd, J =.,.
13 Hz, H),. (m, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,. (q, J =. Hz),. (q, J =. Hz),.,. (q, J =. Hz),. (q, J =. Hz),.. IR (KBr, cm ):,,,,,. HRM (EI) (m/z): calcd for C H F [M+H] + :., found:.. -Benzyl--methylbenzo[d]thiazole (r). Yellow solid, yield mg (%), mp ºC. H MR ( MHz, CDCl ) δ. (s, H),. (s, H),. (m, H),. (d, J =. Hz, H),. (s, H),. (s, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. Benzo[d]thiazol-yl(phenyl)methanone (). White solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (dt, J =.,. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H ao [M+a] + :., found:.. -(-Phenylbut-en-yl)benzo[d]thiazole (). Yellow oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (m, H),. (m, H),. (ddt, J =.,.,. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (t, J =. Hz, H),. (dt, J =.,. Hz, H),. (dt, J =.,. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. (E)-(,-Diphenylvinyl)benzo[d]thiazole (). Yellow solid, yield mg (%), mp - ºC. H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (s, H),. (d, J =. Hz, H),.-. (m, H),. (dt, J =.,. Hz, H),. (t, J =. Hz, H),.-. (m, H),. (dt, J =.,. Hz, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,
![.. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. [D ]-benzylbenzo[d]thiazole (d -a). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.](/docs-images/88/115462758/images/14-1.jpg ",. Hz, H),. (m, H),. (m, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,. HRM (EI) (m/z): calcd for C H D [M+H] + :., found:.. G. References. H. terckx, J. De Houwer, C.")
14 .. IR (KBr, cm ):,,,,,,,. HRM (EI) (m/z): calcd for C H [M+H] + :., found:.. [D ]-benzylbenzo[d]thiazole (d -a). Brown oil, yield mg (%). H MR ( MHz, CDCl ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (m, H),. (m, H). C MR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. IR (KBr, cm ):,,,,,. HRM (EI) (m/z): calcd for C H D [M+H] + :., found:.. G. References. H. terckx, J. De Houwer, C. Mensch, I. Caretti, K. A. Tehrani, W. A. Herrebout,. Van Doorslaer, B. U. W. Maes, Chem. ci.,,,.. (a) G. Kaupp, D. Lübben, O. auerland, Phosphorus, ulfur, and ilicon,,, -. (b) G. Kaupp, Chem. Ber.,,,. H. X-ray Diffraction Parameters and Data for d d Br X-ray of d Table Crystal data and structure refinement for d. Identification code Empirical formula d C H Br Formula weight. Temperature/K.() Crystal system triclinic pace group P a/å.() b/å.() c/å.() α/.()
15 β/.() γ/.() Volume/Å.() Z ρ calc g/cm. μ/mm. F(). Crystal size/mm... Radiation CuKα (λ =.) Θ range for data collection/. to. Index ranges - h, - k, - l Reflections collected Independent reflections [R int =., R sigma =.] Data/restraints/parameters // Goodness-of-fit on F. Final R indexes [I>=σ (I)] R =., wr =. Final R indexes [all data] R =., wr =. Largest diff. peak/hole / e Å./-.
16 I. MR pectra H MR ( MHz, CDCl ) spectrum of compound a f (ppm) C MR ( MHz, CDCl ) spectrum of compound a f (ppm)
17 H MR ( MHz, CDCl ) spectrum of compound b f (ppm) C MR ( MHz, CDCl ) spectrum of compound b
18 H MR ( MHz, CDCl ) spectrum of compound c f (ppm) C MR ( MHz, CDCl ) spectrum of compound c
19 H MR ( MHz, CDCl ) spectrum of compound d O C MR ( MHz, CDCl ) spectrum of compound d
20 H MR ( MHz, CDCl ) spectrum of compound e Cl C MR ( MHz, CDCl ) spectrum of compound e
21 H MR ( MHz, CDCl ) spectrum of compound f C MR ( MHz, CDCl ) spectrum of compound f
22 H MR ( MHz, CDCl ) spectrum of compound g C MR ( MHz, CDCl ) spectrum of compound g
23 H MR ( MHz, CDCl ) spectrum of compound h C MR ( MHz, CDCl ) spectrum of compound h
24 H MR ( MHz, CDCl ) spectrum of compound i f (ppm) C MR ( MHz, CDCl ) spectrum of compound i
25 H MR ( MHz, CDCl ) spectrum of compound j C MR ( MHz, CDCl ) spectrum of compound j
26 H MR ( MHz, CDCl ) spectrum of compound k C MR ( MHz, CDCl ) spectrum of compound k
27 H MR ( MHz, CDCl ) spectrum of compound l C MR ( MHz, CDCl ) spectrum of compound l
28 H MR ( MHz, CDCl ) spectrum of compound m F C MR ( MHz, CDCl ) spectrum of compound m
29 H MR ( MHz, CDCl ) spectrum of compound n Br C MR ( MHz, CDCl ) spectrum of compound n
30 H MR ( MHz, CDCl ) spectrum of compound o O - C MR ( MHz, CDCl ) spectrum of compound o
31 H MR ( MHz, CDCl ) spectrum of compound p F F F C MR ( MHz, CDCl ) spectrum of compound p
32 H MR ( MHz, CDCl ) spectrum of compound q C MR ( MHz, CDCl ) spectrum of compound q
33 H MR ( MHz, CDCl ) spectrum of compound r Cl C MR ( MHz, CDCl ) spectrum of compound r
34 H MR ( MHz, CDCl ) spectrum of compound s O O - C MR ( MHz, CDCl ) spectrum of compound s
35 H MR ( MHz, CDCl ) spectrum of compound t Cl Cl - C MR ( MHz, CDCl ) spectrum of compound t
36 H MR ( MHz, CDCl ) spectrum of compound u Cl F C MR ( MHz, CDCl ) spectrum of compound u
37 H MR ( MHz, CDCl ) spectrum of compound a C MR ( MHz, CDCl ) spectrum of compound a
38 H MR ( MHz, CDCl ) spectrum of compound b C MR ( MHz, CDCl ) spectrum of compound b
39 H MR ( MHz, CDCl ) spectrum of compound c F C MR ( MHz, CDCl ) spectrum of compound c
40 H MR ( MHz, CDCl ) spectrum of compound d Br C MR ( MHz, CDCl ) spectrum of compound d
41 H MR ( MHz, CDCl ) spectrum of compound e O C MR ( MHz, CDCl ) spectrum of compound e
42 H MR ( MHz, CDCl ) spectrum of compound f C MR ( MHz, CDCl ) spectrum of compound f
43 H MR ( MHz, DMO-d ) spectrum of compound g C MR ( MHz, DMO-d ) spectrum of compound g
44 H MR ( MHz, DMO-d ) spectrum of compound h C MR ( MHz, DMO-d ) spectrum of compound h
45 H MR ( MHz, DMO-d ) spectrum of compound i C MR ( MHz, DMO-d ) spectrum of compound i
46 H MR ( MHz, DMO-d ) spectrum of compound j C MR ( MHz, DMO-d ) spectrum of compound j
47 H MR ( MHz, DMO-d ) spectrum of compound k C MR ( MHz, DMO-d ) spectrum of compound k
48 H MR ( MHz, DMO-d ) spectrum of compound l C MR ( MHz, DMO-d ) spectrum of compound l
49 H MR ( MHz, CDCl ) spectrum of compound m C MR ( MHz, CDCl ) spectrum of compound m
50 H MR ( MHz, CDCl ) spectrum of compound n C MR ( MHz, CDCl ) spectrum of compound n
51 H MR ( MHz, CDCl ) spectrum of compound o C MR ( MHz, CDCl ) spectrum of compound o
52 H MR ( MHz, CDCl ) spectrum of compound p F C MR ( MHz, CDCl ) spectrum of compound p
53 H MR ( MHz, CDCl ) spectrum of compound q F F F C MR ( MHz, CDCl ) spectrum of compound q
54 H MR ( MHz, CDCl ) spectrum of compound r C MR ( MHz, CDCl ) spectrum of compound r
55 H MR ( MHz, CDCl ) spectrum of compound O C MR ( MHz, CDCl ) spectrum of compound
56 H MR ( MHz, CDCl ) spectrum of compound C MR ( MHz, CDCl ) spectrum of compound
57 H MR ( MHz, CDCl ) spectrum of compound C MR ( MHz, CDCl ) spectrum of compound
58 H MR ( MHz, CDCl ) spectrum of compound d -a C MR ( MHz, CDCl ) spectrum of compound d -a
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Pd-Catalyzed C-H Activation/xidative Cyclization of Acetanilide with orbornene:
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information Palladium-Catalyzed Oxidative Allylation of Bis[(pinacolato)boryl]methane:
Supporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
Supporting Information
Supporting Information Enantioselective Synthesis of 3-Alkynyl-3-Hydroxyindolin-2-ones by Copper-Catalyzed Asymmetric Addition of Terminal Alkynes to Isatins Ning Xu, Da-Wei Gu, Jing Zi, Xin-Yan Wu, and
N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
![N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides](/thumbs/85/92425281.jpg "N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides")
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
Supporting Information. Cu(I)-Catalyzed Three-Component Reaction of Diazo. Compound with Terminal Alkyne and Nitrosobenzene for
Supporting Information of Cu(I)-Catalyzed Three-Component Reaction of Diazo Compound with Terminal Alkyne and Nitrosobenzene for the Synthesis of Trifluoromethyl Dihydroisoxazoles Xinxin Lv, Zhenghui Kang,
Supporting Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H
Ligand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst
Supporting Information Ligand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst Man Wang, Bizhen Yuan, Tongmei Ma, Huanfeng Jiang and Yingwei Li* School
Supplementary Information. Direct difunctionalization of alkynes with sulfinic acids and
Electronic upplementary Material (E) for RC Advances. This journal is The Royal ociety of Chemistry 204 upplementary nformation Direct difunctionalization of alkynes with sulfinic acids and melecular iodine:
Carbonylative Coupling of Allylic Acetates with. Arylboronic Acids
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
Poly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor
Supporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino
Silver-Catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles
Supporting Information for Silver-Catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles Guichun Fang, a, Jianquan Liu a,c, Junkai Fu,* a Qun Liu, a and Xihe
Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman
A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one
A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one Haoyue Xiang and Chunhao Yang* State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy
Supporting Information
Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
Zn-Catalyzed Diastereo- and Enantioselective Cascade. Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles:
Zn-Catalyzed Diastereo- and Enantioselective Cascade Reaction of 3-Isothiocyanato xindoles and 3-itroindoles: tereocontrolled yntheses of Polycyclic pirooxindoles Jian-Qiang Zhao,, Zhi-Jun Wu, Ming-Qiang
Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous
Synthesis of Cyclopentadienyl Alkyl Ethers via Pd-Catalyzed. Cyclotrimerization of Diarylacetylenes
Synthesis of Cyclopentadienyl Alkyl Ethers via Pd-Catalyzed Cyclotrimerization of Diarylacetylenes Ranran Cai, a Mengmeng Huang, *a Xiuling Cui, a Jianye Zhang, a Chenxia Du, a Yusheng Wu, b and Yangjie
Hualong Ding, Songlin Bai, Ping Lu,* Yanguang Wang*
Supporting Information for Preparation of 2-Amino-3-arylindoles via Pd-Catalyzed Coupling between 3-Diazoindolin-2-imines and Arylboronic Acids as well as Their Extension to 3-Aryl-3-fluoroindolin-2-imines
Supporting Information
Supporting Information Substrates as Electron Donor Precursors: Synthesis of Naphtho-Fused Oxindoles via Benzannulation of 2-Halobenzaldehydes and Indolin-2-ones Feng-Cheng Jia, Cheng Xu, Zhi-Wen Zhou,
Electronic Supplementary Information
Electronic Supplementary Information Regiodivergent Heterocyclization: A Strategy for the Synthesis of Substituted Pyrroles and Furans Using α-formyl Ketene Dithioacetals as Common Precursors Ting Wu,
Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary
![Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary](/thumbs/84/89552735.jpg "Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary")
Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources Changqing Rao, Shaoyu Mai and Qiuling Song* Institute of Next
Supporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
Supporting Information
ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei
A new route for the synthesis of highly substituted 4- aminoquinoline drug like molecules via aza hetero-diels-alder reaction
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Organic & Biomolecular Chemistry Electronic Supplementary Information (ESI)
David L. Davies,*, 1 Charles E. Ellul, 1 Stuart A. Macgregor,*, 2 Claire L. McMullin 2 and Kuldip Singh. 1. Table of contents. General information
Experimental Supporting Information for Experimental and DFT Studies Explain Solvent Control of C-H Activation and Product Selectivity in the Rh(III)-Catalyzed Formation of eutral and Cationic Heterocycles
Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles
Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to Vinyl Sulfone: An Organocatalytic Access to Chiral 3-Fluoro-3-Substituted Oxindoles Xiaowei Dou and Yixin Lu * Department of Chemistry & Medicinal
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol
Supplementry Information for
Supplementry Information for Cyclopropenium ion catalysed Beckmann rearrangement Vishnu P. Srivastava, Rajesh Patel, Garima and Lal Dhar S. Yadav* Department of Chemistry, University of Allahabad, Allahabad,
Supporting Information
Supporting Information Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers Jian-Bo Liu, Xiu-Hua Xu, and Feng-Ling Qing Table of Contents 1. General Information --------------------------------------------------------------------------2
Electronic Supporting Information For. Accessing Heterobiaryls through Transition Metal-Free C-H Functionalization. Content
Electronic Supporting Information For Accessing Heterobiaryls through Transition Metal-Free C-H Functionalization Ananya Banik, Rupankar Paira*,, Bikash Kumar Shaw, Gonela Vijaykumar and Swadhin K. Mandal*,
Supporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using
Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline
![Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline](/thumbs/91/107042141.jpg "Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline")
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal
Supporting Information:
Supporting Information: An rganocatalytic Asymmetric Sequential Allylic Alkylation/Cyclization of Morita-Baylis-Hillman Carbonates and 3-Hydroxyoxindoles Qi-Lin Wang a,b, Lin Peng a, Fei-Ying Wang a, Ming-Liang
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2019 Supporting Information Difluorocarbene-derived trifluoromethylselenolation of benzyl halides Xin-Lei
Supporting Information
Supporting Information for Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF 3 Xueliang Jiang 1 and Feng-Ling Qing* 1,2 Address: 1 Key Laboratory of Organofluorine
Aluminum Foil: A Highly Efficient and Environment- Friendly Tea Bag Style Catalyst with High TON
Supporting Information Pd @ Aluminum Foil: A Highly Efficient and Environment- Friendly Tea Bag Style Catalyst with High TON Fan Lei, Yi Rong, Yu Lei,* Wu Yulan, Chen Tian, and Guo Rong General Remarks.
Halogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations
Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations Drew R. Heitz, John C. Tellis, and Gary A. Molander* Roy and Diana Vagelos Laboratories, Department of Chemistry,
Supporting Information
Gold(I) Catalyzed Intra and Intermolecular Alkenylations of β Yne Pyrroles: Facile Formation of Fused Cycloheptapyrroles and Functionalized Pyrroles Bin Pan, Xiaodong Lu, Chunxiang Wang, Yancheng Hu, Fan
A Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
Electronic Supplementary Information (12 pages)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie
Supplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
[Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents
![[Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents](/thumbs/96/127707581.jpg "[Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents")
[Ag-Ag] 2+ Unit-Encapsulated Trimetallic Cages: One-pot Syntheses and Modulation of Argentophilic Interactions by the Uncoordinated Substituents Guo-Xia Jin,,a Gui-Ying Zhu,,a Yan-Yan Sun, c Qing-Xiu Shi,
Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions
SUPPORTIG IFORMATIO Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions Alexey Volkov, a Fredrik Tinnis, a and Hans Adolfsson.* a a Department of Organic Chemistry,
Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes SUPPORTING INFORMATION
Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes Guo-Lin Gao,, Wujiong Xia, Pankaj Jain and Jin-Quan Yu *, Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey
Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles
Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 Supplementary Material (ESI)
Supporting Information
Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
Efficient Pd-Catalyzed Amination of Heteroaryl Halides
1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting
Supporting Information. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation. of Sulfoxonium Ylides. Xingwei Li*, Table of Contents
Supporting Information Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides Youwei Xu,, Xifa Yang,, Xukai Zhou,, Lingheng Kong,, and Xingwei Li*, Dalian Institute of Chemical
Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a Pharmacologically Active Molecule
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a
Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Lithium Triethylborohydride-Promoted Generation of α,α-difluoroenolates
Trisulfur Radical Anion as the Key Intermediate for the. Synthesis of Thiophene via the Interaction between Elemental.
Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu Guoting Zhang, a Hong Yi, a Hong Chen, a Changliang Bian a Chao Liu
Supporting Information. Efficient N-arylation and N-alkenylation of the five. DNA/RNA nucleobases
Supporting Information Efficient -arylation and -alkenylation of the five DA/RA nucleobases Mikkel F. Jacobsen, Martin M. Knudsen and Kurt V. Gothelf* Center for Catalysis and Interdisciplinary anoscience
Supporting Information. Indole Synthesis via Cobalt(III)-Catalyzed Oxidative Coupling of N-Arylureas and Internal Alkynes
Supporting Information Indole Synthesis via Cobalt(III)-Catalyzed Oxidative Coupling of N-Arylureas and Internal Alkynes Zhuo-Zhuo Zhang, Bin Liu, Jing-Wen Xu, Sheng-Yi Yan, Bing-Feng Shi * Department
Dual role of Allylsamarium Bromide as Grignard Reagent and a. Single Electron Transfer Reagent in the One-Pot Synthesis of.
Dual role of Allylsamarium Bromide as Grignard Reagent and a Single Electron Transfer Reagent in the One-Pot Synthesis of Terminal Olefins Ying Li, Yuanyuan Hu and Songlin Zhang* Key Laboratory of Organic
Supporting information. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation.
Supporting information Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation Saithalavi Anas, Alex Cordi and Henri B. Kagan * Institut de Chimie
Supporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting Information Synthesis of Biaryl Sultams Using Visible-Light-Promoted Denitrogenative
Supporting Information
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
Supporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 Tuning the Lewis Acidity of Boranes in rustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
Construction of Vicinal Quaternary Carbon Centers via Cobalt- Catalyzed Asymmetric Reverse Prenylation
Supporting Information Construction of Vicinal Quaternary Carbon Centers via Cobalt- Catalyzed Asymmetric Reverse Prenylation Minghe Sun, Jia-Feng Chen, Shufeng Chen, Changkun Li* Shanghai Key Laboratory
Supporting Information for
Supporting Information for Room Temperature Palladium-Catalyzed Arylation of Indoles icholas R. Deprez, Dipannita Kalyani, Andrew Krause, and Melanie S. Sanford* University of Michigan Department of Chemistry,
SUPPORTING INFORMATION
SUPPORTING INFORMATION For Synthesis of Fluorenone Derivatives through Palladium-Catalyzed Dehydrogenative Cyclization Hu Li, Ru-Yi Zhu, Wen-Juan Shi, Ke-Han He, and Zhang-Jie Shi* Beijing National Laboratory
Ring-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols
Ring-pening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Jumreang Tummatorn, and Gregory B. Dudley, * Department of Chemistry and Biochemistry, Florida State University,
Supporting Information - I: Experimental Procedures and Characterization
Supporting Information - I: Experimental Procedures and Characterization The Direct Reductive Amination of Electron-deficient Amines with Aldehydes: the Unique Reactivity of Re 2 O 7 Catalyst 1 Braja Gopal
New Efficient Delayed-Action Catalysts Based on Guanidine Templates for Polyurethane Synthesis
New Efficient Delayed-Action Catalysts Based on Guanidine Templates for Polyurethane Synthesis Jérome Alsarraf, a Frédéric Robert, a Henri Cramail* b and Yannick Landais* a a CNRS/Univ. Bordeaux, ISM,
Heterogeneously catalyzed selective aerobic oxidative cross-coupling of terminal alkynes and amides with simple copper(ii) hydroxide
Electronic Supplementary Information (ESI) for Heterogeneously catalyzed selective aerobic oxidative cross-coupling of terminal alkynes and amides with simple copper(ii) hydroxide Xiongjie Jin, Kazuya
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United
Organoselenium-Catalyzed Mild Dehydration of Aldoximes: An Unexpected Practical Method for Organonitrile Synthesis
Supporting Information for Organoselenium-Catalyzed Mild Dehydration of Aldoximes: An Unexpected Practical Method for Organonitrile Synthesis Lei Yu,*,,, Hongyan Li, Xu Zhang,, Jianqing Ye, Jianping Liu,
SUPPORTING INFORMATION
Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
Responsive supramolecular polymer formed by orthogonal metal-coordination and cryptand-based host guest interaction
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Responsive supramolecular polymer formed by orthogonal metal-coordination and cryptand-based host
Electronic Supplementary Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Visible light-mediated dehydrogenative
Directed Zincation of Sensitive Aromatics and
1 TMPZn Li: A ew Active Selective Base for the Directed Zincation of Sensitive Aromatics and Heteroaromatics Marc Mosrin and Paul Knochel* Department Chemie & Biochemie, Ludwig-Maximilians-Universität,
Supporting Information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry Supporting Information General Remarks Most of chemicals were purchased from Sigma-Aldrich, Strem,
Supporting Information. High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions
Supporting Information High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions Min Sik Eom, a Jieun Noh b, Han-Sung Kim b, Soyeon
Supporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
Iridium-catalyzed regioselective decarboxylative allylation of. β-ketoacids: efficient construction of γ, δ-unsaturated ketones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction
Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles
Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu
Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes
Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State
Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes via C-H bond activation
Electronic upplementary Material (EI) for ChemComm. This journal is The Royal ociety of Chemistry 2014 Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes
Supporting Information
Supporting Information N-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-derived Ketimines: Access to Chiral Quaternary Aminooxindoles Jianfeng Xu 1, Chengli
Supporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 Supporting Information Palladium-Catalyzed Construction of Spirooxindoles by Arylative Cyclization of 3-( -Disubstituted)allylidene-2-Oxindoles
Indole Functionalization via Photoredox Gold Catalysis
Indole Functionalization via Photoredox Gold Catalysis Sherif J. Kaldas, Alexandre Cannillo, Terry McCallum, and Louis Barriault* Centre for Catalysis Research and Innovation, Department of Chemistry and
Supporting Information
Supporting Information Rhodium-Catalyzed C H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substitued Indoles** Hao Yan, Haolong Wang, Xincheng Li, Xiaoyi Xin,
Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions
upplementary Information Mapping the Transmission Function of ingle-molecule Junctions Brian Capozzi 1, Jonathan Z. Low 2, Jianlong Xia 3, Zhen-Fei Liu 4, Jeffrey B. Neaton 5,6, Luis M. Campos 2, Latha
Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,
Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department
Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides
Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Ashish Thakur, Kainan Zhang, Janis Louie* SUPPORTING INFORMATION General Experimental: All reactions were conducted under an atmosphere