Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd

Size: px
Start display at page:

Download "Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd"

Transcription

1 J. Am. Chem. Soc. Supporting Information Page S1 Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd Adelina Voutchkova, Leah N. Appelhans, Anthony R. Chianese and Robert H. Crabtree Chemistry Department Yale University New Haven, CT 06511, USA. Supporting Information Table of Contents General Methods Procedures and Characterization of Products in Table 1 Procedures and Characterization of Products in Scheme 2 Procedures and Characterization of Products in Scheme 4 Crystallography References S2 S2 S5 S5 S6 S10

2 J. Am. Chem. Soc. Supporting Information Page S2 General Methods All starting materials and reagents were obtained from commercial sources and used as received unless otherwise noted. All reactions were performed under an argon atmosphere using standard Schlenk techniques, and acetonitrile was distilled over calcium hydride. All glassware was dried overnight prior to use. 1 H, 13 C and 31 P NMR spectra were obtained using a Bruker spectrometer operating at 400 MHz. Chemical shifts are reported in ppm with the residual solvent peak as an internal reference. Chloro(η 4-1,5-cyclooctadiene)(1,3-dimethylimidazole-2-ylidene)rhodium(I) (3) A mixture of bis(η 4-1,5-cyclooctadiene)(di-µ-chloro)dirhodium (54 mg, µmol) and dimethyl imidazolium carboxylate (2) (32 mg, µmol) was stirred in acetonitrile (3 ml) for 5 min at room temperature in a Schlenk flask, followed by heating in oil bath at 75 ºC for 20 min under an atmosphere of argon. The reaction mixture was dried in vacuo, and washed three times with diethyl ether. The yellow solid obtained was analytically pure (70 mg, 93%). The reaction has also been carried out in refluxing acetonitrile for 30 min and has afforded comparable yield. 1 H NMR (400 MHz, CDCl 3 ) δ 6.72 (s, 2H, NCH), 4.94 (m, 2H, COD CH), 4.02 (s, 6H, CH 3 ), 3.22 (m, 2H, COD CH), 2.34 (m, 4H, COD CH 2 ), 1.88 (m, 4H, COD CH 2 ). 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ (d, 1 J Rh C = 50.9 Hz, NCN), (NCH), (d, 1 J Rh C = 6.9 Hz, COD CH), (d, 1 J Rh C = 14.6 Hz, COD CH), (CH 3 ), (d, 1 J Rh C = 1.0 Hz, COD CH2), (COD CH 2 ). These NMR data are consistent with those reported in the literature. 1 Chloro(η 4-1,5-cyclooctadiene)(1,3-dimethylimidazole-2-ylidene)iridium(I) (4) This compound was synthesized following the above procedure with bis(η 4-1,5- cyclooctadiene)(di-µ-chloro)diiridium (60 mg, 89.2 µmol) and dimethyl imidazolium carboxylate (2) (26 mg, µmol). After 20 min. of heating (oil bath, 75 ºC) the color of the solution had changed from red to orange. The reaction mixture was cooled and the solvent removed to dryness in vacuo. The product was obtained by dissolving the solid in

3 J. Am. Chem. Soc. Supporting Information Page S3 dichloromethane and recrystallizing by addition of ether to yield a microcrystalline solid. An orange solid was obtained (63 mg, 82%). 1 H NMR (400 MHz, CDCl 3 ) δ 6.97 (s, 2H, NCH), 4.35 (m, 2H COD CH), 3.89 (s, 6H, CH 3 ), 2.99 (m, 2H, COD CH), 2.20 (m, 4H, COD CH 2 ), (m, 4H, COD CH 2 ). 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ (s, NCN), (s, NCH), 83.64, 53.28, 31.02, (s, COD), (NCH 3 ). These NMR data are consistent with those reported in the literature. *1 Dichloro(1,3-dimethylimidazole-2-ylidene)(p-cymene)ruthenium(II) (6) Di-µ-chlorobis[p-cymene)chlororuthenium(II) (5) was obtained from Strem Chemicals (Newburyport, MA USA) and was used as received. A dry Schlenk tube was charged with 5 (60 mg, 98.3 µmol) and 2 (27 mg, µmol) dissolved in 4 ml acetonitrile. The reaction was stirred for 10 minutes at room temperature, then heated in an oil bath at 75 ºC for 2 hours. It was allowed to cool and excess 2 was filtered from the reaction mixture. The filtrate was then concentrated to dryness under in vacuo and recrystallized from 1:3 CH 2 Cl 2 /ether to afford compound 6 as orange-red needles (66 mg, 85%). 1 H NMR (400 MHz, CDCl 3 ) δ: 6.97 (s, 2H, NCH), 5.41 (d, 3 J = 5.8 Hz, 2H), 5.13 (d, 3 J = 5.8 Hz, 2H), 2.68 (sept, 3 J = 6.8 Hz, 1H), 2.02 (s, 3H, methyl) 3.96 (s, 6H, CH 3 ), 1.22 (d, 3 J = 6.8 Hz, 6H, methyl). 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ : , , 84.68, 82.20, 39.51, 30.78, 22.46, These NMR data are consistent with those reported in the literature. 1 (η 4-1,5-cyclooctadiene)(bis-1,3-dimethylimidazole-2-ylidene)iridium(I) hexafluorophosphate (8) Compound 7 (114 mg, µmol) and 2 (41 mg, µmol) were dissolved in acetonitrile (4 ml) in a 10-mL Schlenk flask protected from light with aluminum foil. This reaction mixture was stirred vigorously for 10 min at room temperature and was then heated in oil bath (75 ºC, 2 h), after which it was allowed to cool and the solution was filtered to remove excess imidazolium carboxylate, after which it was concentrated to dryness in vacuo. The solid was dissolved in 2 ml methylene chloride and was * The literature 1H NMR shifts for COD were reported for CDCl 3 solution as δ:5.23, 4.2, 1.89, However in our hands we have found different values, reported above. All other spectroscopic data for this compound are in agreement with the published data. 1

4 J. Am. Chem. Soc. Supporting Information Page S4 purified by column chromatography by elution with 4:1 hexane/ethyl acetate. A bright orange fraction was eluted with a solution of KPF 6 (1 eq) in acetone. Crystallization of this fraction from 1:3 CH 2 Cl 2 /diethyl ether yielded compound 8 as orange prisms (68 mg, 84 %). 1 H NMR (400 MHz, CDCl 3 ) δ: 7.10 (s, 4H, NCH), 3.89 (s, 6H, CH 3 ), 3.72 (br m, 4H, COD CH), 2.10 (br m, 4H, COD CH 2 ), 1.89 (br m, 4H, COD CH 2 ). 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ: (s, NCN), (s, NCH), 77.22, (s, COD) (s, NCH 3 ). 31 P NMR (162 MHz, CDCl 3 ) δ: (PF 6 ). Analysis calculated for C 20 H 36 F 6 IrN 4 P 2 : C, 33.91%; H, 4.43%; N, 8.79%. Found: C, 34.06%; H, 4.53%, N, 8.84%. Complex 8 was also made by an analogous procedure using 9 rather than 7. Acetato(tris-1,3-dimethylimidazole-2-ylidene)palladium(II) acetate (10) A 10-mL Schlenk flask was charged with Pd(OAc) 2 (109 mg, µmol) and 2 (274 mg, 1.94 mmol). Acetonitrile (7 ml) was added under an inert atmosphere, and the reaction mixture was heated in a 75 ºC oil bath for 12 h. The solution turned yellow then pale yellow during the course of the reaction. It was then cooled and filtered through Celite, after which the filtrate was concentrated to dryness in vacuo and washed twice with ether. The product was recrystallized twice from from 1:3 CH 2 Cl 2 /diethyl ether to yield light yellow prisms of 10 (177 mg, 71%). 1 H NMR (400 MHz, d 6- DMSO) δ: 7.37 (s, 2H, central NCH), 7.30 (s, 4H, wing NCH), 3.73 (s, 12H, wing CH 3 ), 3.55 (s, 6H, central CH 3 ), 3.20 (br s, 6H, H 2 O) 1.60 (s, 3H, O 2 CCH 3, bound) 1.49 (s, 3H, O 2 CCH 3, unbound). 13 C { 1 H} NMR (100 MHz, d 6- DMSO) δ: (s, NCN), (s, NCN), (s, NCH), (s, NCH ), (s, NCH 3 ), (s, NCH 3 ) (s, OAc), (s, OAc ). Analysis calculated for C 19 H 33 N 6 O 4 Pd 3.5H 2 O: C, 39.43%; H, 6.97%; N, 14.51%. Found: C, 39.26%; H, 6.36%, N, 14.51%.

5 J. Am. Chem. Soc. Supporting Information Page S5 Procedures and Characterization of Products in Scheme 2 N,N -dimethylimidazolium-2-carboxylate (2) This product was prepared as previously reported 2 to give a yield of 78%. 1 H NMR (500 MHz, D 2 O) δ 3.82 (s, 6H, N-CH 3 ), 7.26 ppm (s, 2H, H-4 and H-5). 13 C{ 1 H} NMR (400 MHz, D 2 O) δ 36.58, , , Procedures and Characterization of Products in Scheme 4 Chloro(η 4-1,5-cyclooctadiene)(1,3-dimesitylimidazole-2-ylidene)rhodium(I) (12) A 25mL-round-bottom flask was charged with N,N -2,4,6-trimethylphenyl imidazolium chloride (50 mg, µmol) and sodium hydride (60% suspension in mineral oil), (8 mg, 189 µmol). The flask was then charged with dry acetonitrile (10 ml) and stirred in an ice bath for 5 minutes, after which isobutyl chloroformate (0.60 ml, 440 µmol) was added dropwise through a syringe over the course of 10 min. The reaction was allowed to stir in an ice bath for an additional hour, then at room temperature for 6 h. The reaction mixture was then filtered and dried in vacuo to give a light yellow oil which was washed with ether three times. The resulting oil contained 78% 11 by NMR along with the corresponding imidazolium salt, and the mixture was used without further purification. After taking up the oil in 5 ml acetonitrile, [Rh(cod)Cl] 2 (57 mg, 114 µmol) was added and the reaction was refluxed for 2 h. The solution was cooled, and the solvent removed in vacuo. The resulting solid was redissolved in methylene chloride (2 ml), and subjected to column chromatography with 80/20 ethyl acetate/hexanes to afford a yellow solid after evaporation of solvent. It was recrystallized from methylene chloride/pentane (1:3) to afford pure product (0.49 g, 62%). 1 H NMR (400 MHz, CDCl 3 ) δ: 7.06 (s, 4H Mes), 6.99 (s, 2H NHC), 4.42 (s, 2H COD) 3.30 (s, 2H COD), 2.32 (s, 6H CH 3 ), 2.36 (s, 6H CH 3 ), 2.14 (s, 6H CH 3 ), 1.81 (m, 4H COD), 1.58 (m, 4H COD); 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ: 18.5, 20.0, 21.4, 28.9, 33.2, 68.7 (d, 1 J Rh-C = 14.3 Hz), 96.3 (d, 1 J Rh-C = 7.6 Hz), 124.3, 128.8, 129.8, 135.1, 137.0, 137.9, 139.2, (d, 1 J Rh-C = 52.5 Hz). These NMR data are consistent with those reported in the literature. 3

6 J. Am. Chem. Soc. Supporting Information Page S6 Crystallography Structural Description The compound crystallized in the monoclinic space group P2 1 /c with one molecule in the asymmetric unit and four molecules in the unit cell. The geometry about the palladium atom is square planar (planar deviation = Å) with C-Pd(1)-O(1) angles of 87.67(11), (11), and 91.36(11) for C(1), C(6) and C(11) respectively. The heterocyclic carbene ligands are offset from the palladium coordination plane by 66.9, 69.0, and 58.4 for C(1), C(6) and C(11) respectively. The coordinated acetate counter-ion is offset from the same plane by These features are better illustrated in Figure 3. The palladium complex co-crystallized with H 2 O in a ratio of 1:3. The six crystallographically unique aqua-protons were located from the electron difference map and refined with isotropic displacement parameters. For ease of refinement, the O-H bond distances were fixed to a distance of 1.00 Å. Extensive hydrogen bonding is present in the lattice as illustrated in Figures 4 6. Within each unique crystallographic unit, the continuous chain of hydrogen bonding begins with the coordinated acetate counter-ion, continues through two molecules of H 2 O, the free acetate counter-ion, and a final molecule of H 2 O. Intermolecular O-O distances are measured at 2.73, 2.77, 2.76, and 2.74 Å for O(2) O(5), O(5) O(6), O(6) O(4), and O(3) O(7) respectively. Adjacent molecules form hydrogen-bonding dimers possessing a 12-membered ring motif between the corresponding palladium complexes as illustrated in Figure 5. Furthermore, adjacent dimers form hydrogen-bonding tetramers via an eight-member ring as illustrated in Figure 6. Ultimately, propagation of these hydrogen-bonding interactions creates infinite chains along the crystallographic a-axis as illustrated in Figure 7. ORTEPs, packing diagrams and full crystallographic tables follow.

7 Figure 1 J. Am. Chem. Soc. Supporting Information Page S7 Figure 2

8 J. Am. Chem. Soc. Supporting Information Page S8 Figure 3 Figure 4

9 J. Am. Chem. Soc. Supporting Information Page S9 Figure 5 Figure 6

10 J. Am. Chem. Soc. Supporting Information Page S10 Figure 7 References: (1) Herrmann, W. A.; Elison, M.; Fischer, J.; Koecher, C.; Artus, G. R. J. Chem. Eur. J. 1996, 2, (2) Holbrey, J.D.; Reichert W.M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi I.; Rogers R.D. Chem.Commun. 2003, (3) Seayad, A. M.; Selvakumar, K.; Ahmed, M.; Beller, M. Tet. Lett. 2003, 44,

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

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

More information

Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes

Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes Shanmuganathan Saravanakumar, a Markus K. Kindermann, a Joachim

More information

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source

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

More information

Supporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of

Supporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of Supporting Information for Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-mic ligand. Study of the electronic properties and catalytic activities Carmen Mejuto 1, Beatriz Royo

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

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*,,

More information

Syntheses and Structures of Mono-, Di- and Tetranuclear Rhodium or Iridium Complexes of Thiacalix[4]arene Derivatives

Syntheses and Structures of Mono-, Di- and Tetranuclear Rhodium or Iridium Complexes of Thiacalix[4]arene Derivatives Supplementary Information Syntheses and Structures of Mono-, Di- and Tetranuclear Rhodium or Iridium Complexes of Thiacalix[4]arene Derivatives Kenji Hirata, Toshiaki Suzuki, Ai Noya, Izuru Takei and Masanobu

More information

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) 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

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

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:

More information

Supporting Information

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

More information

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain

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

More information

Supporting Information Experimental details

Supporting Information Experimental details Reaction of Elemental Chalcogens with Imidazolium Acetates to Yield Imidazole-2- chalcogenones: Direct Evidence for Ionic Liquids as Proto-Carbenes Héctor Rodríguez, Gabriela Gurau, John D. Holbrey and

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe

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

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Unmasking Representative Structures of TMP-Active Hauser and Turbo Hauser Bases Pablo García-Álvarez, David V. Graham,

More information

Supporting Information For:

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

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

How to build and race a fast nanocar Synthesis Information

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,

More information

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

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

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide 217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

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,

More information

Efficient Pd-Catalyzed Amination of Heteroaryl Halides

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

More information

Diastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines

Diastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines Supporting Information for Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines Alexander Penger, Cortney. von ahmann, Alexander S. Filatov and John T. Welch* Address:

More information

Supporting Information

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

More information

Simplified platensimycin analogues as antibacterial agents

Simplified platensimycin analogues as antibacterial agents Simplified platensimycin analogues as antibacterial agents Dragan Krsta, a Caron Ka, a Ian T. Crosby, a Ben Capuano a and David T. Manallack a * a Medicinal Chemistry and Drug Action, Monash Institute

More information

Electronic Supplementary Information

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,

More information

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien

More information

Supporting Information

Supporting Information Supporting Information New Hexaphosphane Ligands 1,3,5-C 6 H 3 {p-c 6 H 4 N(PX 2 ) 2 } 3 [X = Cl, F, C 6 H 3 OMe(C 3 H 5 )]: Synthesis, Derivatization and, Palladium(II) and Platinum(II) Complexes Sowmya

More information

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov 1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv

More information

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 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

More information

C-H Activation Reactions of Ruthenium N-Heterocyclic Carbene. Complexes: Application in a Catalytic Tandem Reaction Involving C-C

C-H Activation Reactions of Ruthenium N-Heterocyclic Carbene. Complexes: Application in a Catalytic Tandem Reaction Involving C-C SUPPORTING INFORMATION C-H Activation Reactions of Ruthenium N-Heterocyclic Carbene Complexes: Application in a Catalytic Tandem Reaction Involving C-C Bond Formation from Alcohols Suzanne Burling, Belinda

More information

Supporting Information

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

More information

Supporting Information

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

More information

Supporting Information

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,

More information

Supporting Information

Supporting Information Supporting Information for Macromol. Chem. Phys, DOI: 10.1002/macp.201700302 Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions Ansgar Sehlinger,

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

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

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Halogen halogen interactions in diiodo-xylenes

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

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information for uminum complexes containing salicylbenzoxazole

More information

Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions

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

More information

Photolysis for Vitamin D Formation. Supporting Information

Photolysis for Vitamin D Formation. Supporting Information S1 Synthesis of 1α-Hydroxyvitamin D 5 Using a Modified Two Wavelength Photolysis for Vitamin D Formation Supporting Information Robert M. Moriarty and Dragos Albinescu Spectra 1. 13 C: 3β-Acetoxy-stigmasta-5,7-diene

More information

Supporting Information

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

More information

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex

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

More information

Supporting Information

Supporting Information Supporting Information Tris(2-dimethylaminoethyl)amine: A simple new tripodal polyamine ligand for Group 1 metals David M. Cousins, Matthew G. Davidson,* Catherine J. Frankis, Daniel García-Vivó and Mary

More information

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008 Supplementary Information for: Scrambling Reaction between Polymers Prepared by Step-growth and Chain-growth Polymerizations: Macromolecular Cross-metathesis between 1,4-Polybutadiene and Olefin-containing

More information

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 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

More information

Coupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose.

Coupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. General Experimental Procedures. NMR experiments were conducted on a Varian Unity/Inova 400-MHz Fourier Transform NMR Spectrometer. Chemical shifts are downfield from tetramethylsilane in CDCl 3 unless

More information

Electronic Supporting Information

Electronic Supporting Information Electronic Supporting Information Reactions of Tp(NH=CPh 2 )(PPh 3 )Ru Cl with HC CPh in the presence of H 2 O: Insertion/Hydration Products Chih-Jen Cheng, a Hung-Chun Tong, a Yih-Hsing Lo,* b Po-Yo Wang,

More information

Supporting Information

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

More information

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,

More information

Active Trifluoromethylating Agents from Well-defined Copper(I)-CF 3 Complexes

Active Trifluoromethylating Agents from Well-defined Copper(I)-CF 3 Complexes Supplementary Information Active Trifluoromethylating Agents from Well-defined Copper(I)-CF 3 Complexes Galyna Dubinina, Hideki Furutachi, and David A. Vicic * Department of Chemistry, University of Hawaii,

More information

Supplementary Information: Selective Catalytic Oxidation of Sugar Alcohols to Lactic acid

Supplementary Information: Selective Catalytic Oxidation of Sugar Alcohols to Lactic acid Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Supplementary Information: Selective Catalytic Oxidation of Sugar Alcohols to Lactic acid

More information

3-Bromomethyl pyridine

3-Bromomethyl pyridine M 3 L 2 metallo-cryptophanes: [2]catenane and simple cages James J. Henkelis, Tanya K. Ronson, Lindsay P. Harding and Michaele J. Hardie Supplementary Material Synthesis Chemicals were obtained from commercial

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

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,

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Micro- and mesoporous poly(schiff-base)s

More information

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3 Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

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

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany Sandwich Complexes Containing Bent Palladium ains Yasuki Tatsumi, Katsunori Shirato, Tetsuro Murahashi,* Sensuke Ogoshi and Hideo Kurosawa*

More information

Supporting Information

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

More information

SUPPORTING INFORMATION

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

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

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 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

More information

Supporting Information

Supporting Information Supporting Information Control the Structure of Zr-Tetracarboxylate Frameworks through Steric Tuning Jiandong Pang,,,,# Shuai Yuan,,# Junsheng Qin, Caiping Liu, Christina Lollar, Mingyan Wu,*, Daqiang

More information

Supporting Information for:

Supporting Information for: Supporting Information for: Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: The Effect of The Lifetime of the E Photoenol on the Photochemistry Armands Konosonoks, P. John Wright,

More information

Reduction-free synthesis of stable acetylide cobalamins. Table of Contents. General information. Preparation of compound 1

Reduction-free synthesis of stable acetylide cobalamins. Table of Contents. General information. Preparation of compound 1 Electronic Supporting Information Reduction-free synthesis of stable acetylide cobalamins Mikołaj Chromiński, a Agnieszka Lewalska a and Dorota Gryko* a Table of Contents General information Numbering

More information

Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes

Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes Takahiko Ogawa, a Adam J. Ruddy, a Orson L. Sydora, *,b Mark

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Functional nickel complexes of N-heterocyclic carbene ligands in pre-organized and supported thin film materials

Functional nickel complexes of N-heterocyclic carbene ligands in pre-organized and supported thin film materials Supporting Information Functional nickel complexes of N-heterocyclic carbene ligands in pre-organized and supported thin film materials Xinjiao Wang, a Marek Sobota, b Florian T. U. Kohler, c Bruno Morain,

More information

Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex.

Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex. Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex. Emmanuelle Despagnet-Ayoub, Michael K. Takase, Jay A. Labinger and John E. Bercaw Contents 1. Experimental

More information

[(NHC)Au I ]-Catalyzed Acid Free Hydration of Alkynes at Part-Per-Million Catalyst Loadings

[(NHC)Au I ]-Catalyzed Acid Free Hydration of Alkynes at Part-Per-Million Catalyst Loadings SUPPORTING INFORMATION [(NHC)Au I ]-Catalyzed Acid Free Hydration of Alkynes at Part-Per-Million Catalyst Loadings Nicolas Marion, Rubén S. Ramón, and Steven P. Nolan Institute of Chemical Research of

More information

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence

More information

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. 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

More information

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Electronic supplementary information Strong CIE activity, multi-stimuli-responsive

More information

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. 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

More information

Supporting Information

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

More information

Structure and Reactivity of Unusual N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts.

Structure and Reactivity of Unusual N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts. Structure and Reactivity of Unusual N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts. Hélène Lebel,*, Marc K. Janes, André B. Charette, Steven P. Nolan Département de

More information

Chia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*

Chia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen* Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts

Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for: Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their

More information

Hydrophobic Ionic Liquids with Strongly Coordinating Anions

Hydrophobic Ionic Liquids with Strongly Coordinating Anions Supporting material Hydrophobic Ionic Liquids with Strongly Coordinating Anions Hasan Mehdi, Koen Binnemans*, Kristof Van Hecke, Luc Van Meervelt, Peter Nockemann* Experimental details: General techniques.

More information

Supporting Information

Supporting Information Supporting Information Unprecedented solvent-dependent sensitivities in highly efficient detection of metal ions and nitroaromatic compounds by a fluorescent Ba MOF Rongming Wang, Xiaobin Liu, Ao Huang,

More information

Electronic Supplementary Information for: Photo-reversible surfaces to regulate cell adhesion

Electronic Supplementary Information for: Photo-reversible surfaces to regulate cell adhesion Electronic Supplementary Information for: Photo-reversible surfaces to regulate cell adhesion Alexis Goulet-Hanssens, Karen Lai Wing Sun, Timothy E. Kennedy * and Christopher J. Barrett * Department of

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

Supporting Information. Stable Dioxetane Precursors as Highly Selective. for Singlet Oxygen

Supporting Information. Stable Dioxetane Precursors as Highly Selective. for Singlet Oxygen Supporting Information Stable Dioxetane Precursors as Highly Selective Trap-and-Trigger Chemiluminescent Probes for Singlet Oxygen Laura A. MacManus-Spencer, Douglas E. Latch, Kim M. Kroncke, and Kristopher

More information

Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril

Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril SUPPORTING INFORMATION Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril Lidia Strimbu Berbeci, Wei Wang and Angel E. Kaifer* Center for Supramolecular Science and

More information

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Electronic Supplementary Information (ESI) Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Jie Liu, ab Qing Meng, a Xiaotao Zhang, a Xiuqiang Lu, a Ping

More information

An improved preparation of isatins from indoles

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,

More information

Facile Multistep Synthesis of Isotruxene and Isotruxenone

Facile Multistep Synthesis of Isotruxene and Isotruxenone Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw

More information

Selective total encapsulation of the sulfate anion by neutral nano-jars

Selective total encapsulation of the sulfate anion by neutral nano-jars Supporting Information for Selective total encapsulation of the sulfate anion by neutral nano-jars Isurika R. Fernando, Stuart A. Surmann, Alexander A. Urech, Alexander M. Poulsen and Gellert Mezei* Department

More information

Light irradiation experiments with coumarin [1]

Light irradiation experiments with coumarin [1] Materials and instruments All the chemicals were purchased from commercial suppliers and used as received. Thin-layer chromatography (TLC) analysis was carried out on pre-coated silica plates. Column chromatography

More information

Springloaded porhyrin NHC hybrid rhodium(iii) complexes: carbene dissociation and oxidation catalysis

Springloaded porhyrin NHC hybrid rhodium(iii) complexes: carbene dissociation and oxidation catalysis Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 ELECTRONIC SUPPLEMENTARY INFORMATION Springloaded porhyrin NHC hybrid rhodium(iii) complexes: carbene

More information

A Photocleavable Linker for the Chemoselective Functionalization of Biomaterials

A Photocleavable Linker for the Chemoselective Functionalization of Biomaterials Electronic Supplementary Information A otocleavable Linker for the Chemoselective Functionalization of Biomaterials Liz Donovan and Paul A. De Bank* Department of armacy and armacology and Centre for Regenerative

More information

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Supporting information Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Toni Mäkelä, a Elina Kalenius a and Kari Rissanen a* a University of Jyvaskyla, Department of Chemistry, Nanoscience

More information

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NP 4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NaEt C 10 H 18 4 Na C 2 H 6 C 8 H 12 3 (202.2) (23.0) (46.1) (156.2) Classification Reaction types and substance

More information

SUPPLEMENTARY INFORMATION

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

More information