Supporting Information
|
|
|
- Daniela Garrett
- 5 years ago
- Views:
Transcription
1 Supporting Information Efficient copper-catalyzed coupling of aryl chlorides, bromides and iodides with aqueous ammonia Hanhui Xu and Christian Wolf* Department of Chemistry, Georgetown University, Washington DC, 57 Experimental Procedures General Procedures. All chemicals used were of reagent grade. Flash chromatography was performed on Kieselgel 6, particle size mm. NMR spectra were obtained at 4 MHz ( 1 H NMR) and 1 MHz ( 13 C NMR) using CDCl 3 as solvent unless noted otherwise. Chemical shifts are reported in ppm relative to TMS. General procedure for the Cu-catalyzed amination of aryl halides A 1 ml reaction vessel was charged with Cu 2 O (14.3 mg,.1 mmol), aryl halide (2. mmol), 1.3 ml of N-methyl pyrrolidinone (NMP), 1.3 ml of ammonium hydroxide solution (29% NH 3, 2. mmol) and a magnetic stir bar. The vessel was sealed with a Teflon screw cap, immersed in a preheated oil bath and the reaction mixture was stirred at 8 o C. Upon completion, the reaction mixture was cooled to 25 o C, quenched with water, extracted with diethyl ether and dried over anhydrous MgSO 4. The solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel as described below. General microwave-assisted procedure for the Cu-catalyzed amination of aryl chlorides A mixture of Cu 2 O (14.3 mg,.1 mmol), aryl chloride (2. mmol) and 1.3 ml of N- methyl pyrrolidinone (NMP) was placed with 1.3 ml of ammonium hydroxide solution (29% NH 3, 2. mmol) into a 1 ml glass tube. The reaction mixture was placed in a microwave oven and heated to 11 o C ( W) while the temperature was monitored using a calibrated infrared temperature control. Upon completion, the mixture was allowed to cool to room temperature, quenched with water, extracted with diethyl ether and dried over anhydrous MgSO 4. The solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel as described below. Product identification (yields are corresponding to the reactions of the aryl halides given in Table 1) Aniline. 1 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave 186. mg of a colorless oil (2. mmol, 1%). 1 H NMR: δ 3.54 (s, br, 2H), (m, 2H), (m, 1H), (m, 2H). 13 C NMR: δ 115.2, 118.6, 129.4, S1
2 o-toluidine. 2 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave 25.7 mg of a colorless oil (1.92 mmol, 96%). 1 H NMR: δ 2.9 (s, 3H), 3.47 (s, br, 2H), 6.58 (d, J = 7.6 Hz, 1H), 6.67 (t, J = 7.6 Hz, 1H), (m, 2H). 13 C NMR: δ 17.4, 115., 118.7, 122.4, 127.1, 13.6, p-toluidine. 1 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave 29.7 mg of slight yellow crystals (1.96 mmol, 98%). 1 H NMR: δ 2.19 (s, 3H), 3.4 (s, br, 2H), 6.69 (d, J = 8.4 Hz, 2H), 6.91 (d, J = 8.4 Hz, 2H). 13 C NMR: δ 2.6, 115.4, 127.7, 129.9, ,5-Dimethylaniline. 3 Purification by flash chromatography (hexanes:ethyl acetate =1:1) gave mg of a colorless oil (2. mmol, 1%). 1 H NMR: δ 2.2 (s, 6H), 3.47 (s, br, 2H), 6.27 (s, 2H), 6.91 (s, 1H). 13 C NMR: δ 21.8, 113.7, 121., 139.4, Isopropylaniline. 4 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave mg of a colorless oil (1.64 mmol, 82%). 1 H NMR: δ 1.23 (d, J = 6.8 Hz, 6H), (m, 1H), 3.56 (s, br, 2H), 6.61 (dd, J = 8., 1.2 Hz, 1H), (m, 1H), (m, 1H), 7.11 (dd, J = 7.6, 1. Hz, 1H). 13 C NMR: δ 22.4, 27.7, 115.9, 119.1, 125.5, 126.6, 132.7, Aminobiphenyl. 1 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave mg of slight brown crystals (1. mmol, 75%). 1 H NMR: δ 3.71 (s, br, 2H), (m, 2H), (m, 2H), (m, 5H). 13 C NMR: δ 115.6, 118.6, 127.2, 127.6, 128.5, 128.9, 129.1, 13.5, 139.6, Aminonaphthalene. 1 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave mg of purple crystals (1.8 mmol, 9%). 1 H NMR: δ 4.1 (s, br, 2H), 6.68 (dd, J = 7.2, 1.2 Hz, 1H), (m, 2H), (m, 2H), (m, 2H). 13 C NMR: δ 19.7, 119., 12.9, 123.7, 124.9, 125.9, 126.4, 128.6, 134.5, ,3-Phenylenediamine. 1 Purification by flash chromatography (hexanes:ethyl acetate=9:1) gave 23.3 mg of purple crystals (1.88 mmol, 94%). 1 H NMR: δ 3.55 (s, br, 4H), 5.94 (d, J = 2. Hz, 1H), 6.8 (dd, J = 8., 2. Hz, 2H), 6.91(t, J = 8. Hz, 1H). 13 C NMR: δ 12.5, 16.4, 13.6, Chloroaniline. 5 Purification by flash chromatography (hexanes:ethyl acetate=1:1) gave mg of slight yellow crystals (1.86 mmol, 93%). 1 H NMR: δ 3.66 (s, br, 2H), (m, 1H), 6.6 (t, J = 2. Hz, 1H), 6.69 (dd, J = 8., 2. Hz, 1H), 7.1(t, J = 8. Hz, 1H). 13 C NMR: δ 113.3, 114.9, 118.4, 13.4, 134.8, p-anisidine. 1 Purification by flash chromatography (hexanes:ethyl acetate=9:1) gave mg of slight purple crystals (1.88 mmol, 94%). 1 H NMR: δ 3.41 (s, br, 2H), 3.71 (s, 3H), 6.6 (dd, J = 6.8, 2. Hz, 2H), 6.72 (dd, J = 6.8, 2. Hz, 2H). 13 C NMR: δ 55.7, 114.8, 116.4, 14.1, Aminobenzonitrile. 1 Purification by flash chromatography (hexanes:ethyl acetate=9:1) gave mg of white crystals (1.62 mmol, 81%). 1 H NMR: δ 4.32 (s, br, 2H), 6.64 (dd, J = 6.8, 2. Hz, 2H), 7.37 (dd, J = 6.8, 2. Hz, 2H). 13 C NMR: δ 99.5, 114.4, 12.4, 133.7,.8. 4-Nitroaniline. 6 Purification by flash chromatography (hexanes:ethyl acetate=8:2) gave mg of slight yellow crystals (1.72 mmol, 86%). 1 H NMR: δ 4.4 (s, br, 2H), 6.63 (d, J = 8.8 Hz, 2H), 8.7 (d, J = 8.8 Hz, 2H). 13 C NMR: δ 113.4, 126.3, 139., S2
3 3-Aminoacetophenone. 7 Purification by flash chromatography (hexanes:ethyl acetate=9:1) gave mg of slight yellow crystals (1.84 mmol, 92%). 1 H NMR: δ 2.52 (s, 3H), 4. (s, br, 2H), 6.84 (dd, J = 8., 1.6 Hz, 1H), (m, 3H). 13 C NMR: δ 26.7, 113.9, 118.5, 119.7, 129.4, 138.1, 147.1, Aminobenzaldehyde. 1 Purification by flash chromatography (hexanes:ethyl acetate=7:3) gave mg of slight yellow crystals (1.58 mmol, 79%). 1 H NMR (in (CD 3 ) 2 SO): δ 5.78 (s, br, 2H), 6.66 (d, J = 8.4 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 9.61 (s, 1H). 13 C NMR: δ 113.4, 125.5, 132.2, 154.7, Aminopyridine. 8 Purification by flash chromatography (hexanes:ethyl acetate=7:3) gave mg of white crystals (1.48 mmol, 74%). 1 H NMR (CD 3 OD): δ 5.6 (s, br, 2H), 6.55 (d, J = 6.4 Hz, 2H), 7.95 (d, J = 6.4 Hz, 2H). 13 C NMR: δ 11.3, 149.7, Amino-2-methylquinoline. 9 Purification by flash chromatography (dichloromethane:ethanol:triethylamine=1:1:3) gave mg of white crystals (1.62 mmol, 81%). 1 H NMR: δ 2.58 (s, 3H), 4.74 (s, 2H), 6.49 (s, 1H), 7.38 (m, 1H), 7.6 (m, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H). 13 C NMR: δ 25.2, 13.9, 117.4, 12., 124.1, 129., 129.4, 148.6, 149.6, Ethyl 4-aminobenzoate. 1 Purification by flash chromatography (hexanes:ethyl acetate=8:2) gave mg of slight yellow crystals (1.66 mmol, 83%). 1 H NMR: δ 1.35 (t, J = 7.2 Hz, 3H), 4.16 (s, br, 2H), 4.31 (q, J = 7.2 Hz, 2H), 6.62 (dd, J = 8.8, 2. Hz, 2H), 7.84 (dd, J = 8.8, 2. Hz, 2H). 13 C NMR: δ 14.4, 6.3, 113.7, 119.7, 131.5, 151., Methyl 2-aminobenzoate. 11 Purification by flash chromatography (hexanes:ethyl acetate=8:2) gave mg of slight yellow crystals (1.84 mmol, 92%). 1 H NMR: δ 3.84 (s, 3H), 5.71 (s, br, 2H), 6.62 (t, J = 7.6 Hz, 2H), 7.24 (m, 1H), 7.84 (dd, J = 8.4, 1.6 Hz, 1H). 13 C NMR: δ 51.5, 11.7, 116.2, 116.7, 131.2, 134.1,.5, Aminobenzoic acid. 12 Purification by flash chromatography (hexanes:ethyl acetate=6:4) gave mg of white crystals (1.88 mmol, 94%). 1 H NMR: δ 5.19 (s, br, 2H), (m, 1H), 6.73 (dd, J = 8.8, 2. Hz, 1H), (m, 1H), 7.84 (dd, J = 8.8, 2. Hz, 1H). 13 C NMR: δ 111.9, 116.9, 118., 132.9, 135.3, 152.9, References 1. Cors, A; Bonesi, S. M.; Erra-Balsells, R. Tetrahedron Lett. 8, 49, Rahaim Jr, R. J.; Maleczka Jr., R. E. Synthesis 6, Strazzolini, P.; Misuri, N.; Polese, P. Tetrahedron Lett. 5, 46, Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 6, 128, McLaughlin, M. A.; Barnes, D. M. Tetrahedron Lett. 6, 47, Yusubov, M. S.; Funk, T. V.; Chi, K.; Cha, E.; Kim, G. H.; Kirschning, A.; Zhdankin, V. V. J. Org. Chem. 8, 73, Spencer, J.; Anjum, N.; Patel, H.; Rathnam, R. P.; Verma, J. Synlett 7, Babu, S. N. Narendra; Srinivasa, G. R.; Santhosh, D. C.; Gowda, D. Channe. J. Chem. Res. 4, 1, Zhou, Y.; Li, J.; Liu, H.; Zhao, L.; Jiang, H. Tetrahedron Lett. 6, 47, Gadakh, A. V.; Karale, B. K. Synth. Commun. 8, 38, Fairlamb, I. J. S.; Grant, S.; McCormack, P.; Whittall, J. Dalton Trans. 7, 8, Guin, D.; Baruwati, B.; Manorama, S. V. Org. Lett. 7, 9, S3
4 1 H NMR and 13 C NMR spectra of aniline in CDCl 3 : S4
5 1 H NMR and 13 C NMR spectra of o-toluidine in CDCl 3 : S5
6 1 H NMR and 13 C NMR spectra of p-toluidine in CDCl 3 : S6
7 1 H NMR and 13 C NMR spectra of 3,5-dimethylaniline in CDCl 3 : S7
8 1 H NMR and 13 C NMR spectra of 2-isopropylaniline in CDCl 3 : S8
9 1 H NMR and 13 C NMR spectra of 2-aminobiphenyl in CDCl 3 : S9
10 1 H NMR and 13 C NMR spectra of 1-aminonaphthalene in CDCl 3 : S1
11 1 H NMR and 13 C NMR spectra of 1,3-phenylenediamine in CDCl 3 : S11
12 1 H NMR and 13 C NMR spectra of 3-chloroaniline in CDCl 3 : Cl Cl 1 S12
13 1 H NMR and 13 C NMR spectra of 4-anisidine in CDCl 3 : OMe OMe 1 S13
14 1 H NMR and 13 C NMR spectra of 4-aminobenzonitrile in CDCl 3 : CN CN ppm (t1) 1 S14
15 1 H NMR and 13 C NMR spectra of 4-nitroaniline in CDCl 3 : NO 2 NO 2 ppm (t1) 1 S15
16 1 H NMR and 13 C NMR spectra of 3-aminoacetophenone in CDCl 3 : COMe COMe 1 S16
17 1 H NMR and 13 C NMR spectra of 4-aminobenzaldehyde in d 6 -DMSO: CHO CHO S17
18 1 H NMR and 13 C NMR spectra of 4-aminopyridine in CD 3 OD: N 5.. N 1 S18
19 1 H NMR and 13 C NMR spectra of 4-amino-2-methylquinoline, in CDCl 3 : N N S19
20 1 H NMR and 13 C NMR spectra of ethyl 4-aminobenzoate in CDCl 3 : COOEt COOEt 1 S2
21 1 H NMR and 13 C NMR spectra of methyl 2-aminobenzoate in CDCl 3 : COOMe COOMe 1 S21
22 1 H NMR and 13 C NMR spectra of 2-aminobenzoic acid in CD 3 OD: COOH COOH 1 S22
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
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
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Patrick S. Fier* and Kevin M. Maloney* S1 General experimental details All reactions
Electronic Supplementary Information
Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong
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
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
How to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
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
PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions
S1 Supporting Information PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions Yanan Zhao, a Jian Li, a Chunju Li, a Kun Yin, a Dongyan Ye a and Xueshun Jia*, a, b a Department
Supporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
SUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
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,
An improved preparation of isatins from indoles
An improved preparation of isatins from indoles Jiro Tatsugi,* Tong Zhiwei, and Yasuji Izawa Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, Yachigusa, Yakusa-cho,
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,
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)
SUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles
SUPPRTING INFRMATIN Carbon-Hydrogen Bond Functionalization Approach in the Synthesis of Fluorenones and ortho-arylated Benzonitriles Dmitry Shabashov, Jesús R. Molina Maldonado and lafs Daugulis* Department
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
Table of Contents 1. General procedure for the chiral phosphoric acid catalyzed asymmetric reductive amination using benzothiazoline
Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor Kodai Saito, Takahiko Akiyama* Department of Chemistry, Faculty of Science, Gakushuin University,
Supporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information Merging visible-light photoredox and copper catalysis
Supporting Information
1 Supporting Information Gold-catalyzed Synthesis of 3-arylindoles via Annulation of Nitrosoarenes and Alkynes Siva Murru, August A. Gallo and Radhey S. Srivastava* Department of Chemistry, University
Supporting Information:
Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:
Supporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
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
An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate
A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate 1 Edward J. Hennessy and Stephen L. Buchwald Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting
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
Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012
Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,
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
Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
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:
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
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 For:
Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown
Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones
Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Aurora Martínez-Muñoz, David Monge,* Eloísa Martín-Zamora, Eugenia Marqués-López, Eleuterio Álvarez, Rosario Fernández,*
Bio-based Green Solvent Mediated Disulfide Synthesis via Thiol Couplings Free of Catalyst and Additive
Bio-based Green Solvent Mediated Disulfide Synthesis via Thiol Couplings Free of Catalyst and Additive Yunyun Liu, ab Hang Wang, b Chunping Wang, b Jie-Ping Wan* ab and Chengping Wen* c a Key Laboratory
Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template
Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu
Supplementary Material
10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination
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
Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable
1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was
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
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information for Chiral Brönsted Acid Catalyzed Asymmetric Baeyer-Villiger Reaction of 3-Substituted Cyclobutanones Using Aqueous
Supplementary Table S1: Response evaluation of FDA- approved drugs
SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was
The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004.
The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004. Sterically Bulky Thioureas as Air and Moisture Stable Ligands for Pd-Catalyzed Heck Reactions of
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Content Synthesis of compounds 2a, 2b in Scheme
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
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
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
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
Accessory Information
Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department
Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid
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
Palladium-Catalyzed Alkylarylation of Acrylamides with
Supporting Information Palladium-Catalyzed Alkylarylation of Acrylamides with Unactivated Alkyl Halides Hua Wang, Li-a Guo, and Xin-Hua Duan* Department of Chemistry, School of Science and ME Key Laboratory
dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.
Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with
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
Supplementary Information for. Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines
Supplementary Information for Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines Yujiro Hoshino,* a Moriaki Okuno, a Eri Kawamura, a Kiyoshi Honda, b and Seiichi Inoue
Supporting information. Direct Enantioselective Aldol Reactions catalyzed by a Proline-Thiourea Host- Guest Complex
Supporting information Direct Enantioselective Aldol Reactions catalyzed by a Proline-Thiourea Host- Guest Complex Ömer Reis, Serkan Eymur, Barbaros Reis, Ayhan S. Demir* Department of Chemistry, Middle
Copper Mediated Fluorination of Aryl Iodides
Copper Mediated Fluorination of Aryl Iodides Patrick S. Fier and John F. Hartwig* Department of Chemistry, University of California, Berkeley, California 94720, United States. Supporting Information Table
Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and
Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and
Supporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization
Supporting Information for An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Hang Jiang, Yu Zhang, Dushen Chen, Bo Zhou, and Yanghui Zhang * Department of Chemistry, and Shanghai Key
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: Regioselective esterification of vicinal diols on monosaccharide derivatives via
Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions. Guijun Wang,*Jean Rene Ella-Menye, Michael St. Martin, Hao Yang, Kristopher
Supporting Information
Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in
Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3
S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,
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
Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,
Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
Supporting Information:
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines
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
Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes
Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,
Electronic Supplementary Information
Electronic Supplementary Information Effect of polymer chain conformation on field-effect transistor performance: synthesis and properties of two arylene imide based D-A copolymers Dugang Chen, a Yan Zhao,
Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,
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
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
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:
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
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
Supporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
guanidine bisurea bifunctional organocatalyst
Supporting Information for Asymmetric -amination of -keto esters using a guanidine bisurea bifunctional organocatalyst Minami Odagi* 1, Yoshiharu Yamamoto 1 and Kazuo Nagasawa* 1 Address: 1 Department
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,
Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene
Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:
Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker
Experimental Materials and Methods. All 31 P NMR and 1 H NMR spectra were recorded on 250 MHz Bruker or DRX 500 MHz instruments. All 31 P NMR spectra were acquired using broadband gated decoupling. 31
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
Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones
Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università
An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters
S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan
Supporting Information
Supporting Information One Pot Synthesis of 1,3- Bis(phosphinomethyl)arene PCP/PNP Pincer Ligands and Their Nickel Complexes Wei-Chun Shih and Oleg V. Ozerov* Department of Chemistry, Texas A&M University,
Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
Supporting Information
Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
Supporting Information Reagents. Physical methods. Synthesis of ligands and nickel complexes.
Supporting Information for Catalytic Water Oxidation by A Bio-inspired Nickel Complex with Redox Active Ligand Dong Wang* and Charlie O. Bruner Department of Chemistry and Biochemistry and Center for Biomolecular
Synthesis of Diaryl Selenides using Electrophilic Selenium Species and Nucleophilic Boron Reagents in Ionic Liquids
Synthesis of Diaryl Selenides using Electrophilic Selenium Species and Nucleophilic Boron Reagents in Ionic Liquids Camilo S. Freitas, a Angelita M. Barcellos, a Vanessa G. Ricordi, a Jesus M. Pena, b
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Department of Pharmacology and Pharmaceutical Sciences, School of life sciences
Supporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert
SUPPLEMENTARY INFORMATION
Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
Supporting Information
Supporting Information Rhodium-Catalyzed Annulation Reactions of 2-Cyanophenylboronic Acid with Alkynes and Strained Alkenes Tomoya Miura and Masahiro Murakami* Department of Synthetic Chemistry and Biological
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 208 Supporting Information Cobalt-Catalyzed Regioselective Syntheses of Indeno[2,-c]pyridines
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
J. Am. Chem. Soc. Supporting Information S 1 The First Suzuki Cross-Coupling of Aryltrimethylammonium Salts. Simon B. Blakey and David W. C. MacMillan* Division of Chemistry and Chemical Engineering, California
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