Supporting Information

Size: px
Start display at page:

Download "Supporting Information"

Transcription

1 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, College Station, Texas S1

2 Table of Contents. I. General procedure for screening and optimization of synthesis of 3a-X2 S3 II. Synthesis of tbu (PCP)H by different methods III. C-P Bond cleavage observation in Ph (PCP)H and ipr (PNP) synthesis IV. Control reactions related to the synthesis of ipr (PCP)NiX (6) S4 S6 S8 V. NMR spectra S10 S2

3 I. General procedure for screening and optimization of synthesis of 3a-X2 Table 1, Entry 1~6: In a J. Young NMR tube, the reactin of 1-X (0.20 mmol, 23.0 μl for 1-Cl, 24.0 μl for 1-Br, and 43.6 mg for 1-I) and 2a-X (0.20 mmol, 38.0 μl for 2a-Cl and 54.4 mg for 2a-I) in 0.7 ml of C6D6 (Entry 1) or CD3CN (Entry 2~6) was heated at the required temperature as indicated in Table 1 for 15 h. After the reaction was cooled to room temperature, the conversion was determined by 31 P NMR and 1 H NMR. Table 1, Entry 7~10: In a J. Young NMR tube, to the CD3CN (0.7 ml) solution of 1-Cl (23.0 μl, 0.20 mmol) and 2a-Cl (38.0 μl, 0.20 mmol) was added sodium iodide (30.0 mg, 0.20 mmol for Entry 7; 60.0 mg, 0.40 mmol for Entry 8; 3.00 mg, 0.02 mmol for Entry 9) or lithium bromide (17.4 mg, 0.20 mmol for Entry 10). The mixture was heated at 50 C for 15 h (Entry 7, 8, and 10) or 20 h (Entry 9). After the reaction was cooled to room temperature, the conversion was determined by 31 P NMR and 1 H NMR. S3

4 II. Synthesis of tbu (PCP)H by different methods In a screw-cap culture tube, to the acetonitrile solution (10 ml) of m-xylylene dibromide (4a-Br2, 528 mg, 2.00 mmol) was added di-tert-butylchlorophosphine (2a-Cl, 723 mg, 4.00 mmol), and the reaction mixture was stirred at 100 C for 15 h. After cooling down to room temperature, magnesium powder (122 mg, 5.00 mmol) was added under argon, and the reaction mixture was stirred at 0 C for 2 h. The reaction was allowed to warm to room temperature and stirred overnight. The product was extracted by pentane (3 20 ml), and the volatiles were removed under vacuum, yielding a yellow oil. Isolated yield: 600 mg, 76% (75% purity). * * * * * * * * Impurity 31 P{ 1 H} NMR * Figure S1. 1 H NMR and 31 P{ 1 H} NMR spectra of 5b in C6D6 at RT measured on a 500 MHz Varian NMR spectrometer. S4

5 In a screw cap culture tube, to the acetonitrile solution (10 ml) of m-xylylene dichloride (4a-Cl2, 350 mg, 2.00 mmol) was added 2a-Cl (723 mg, 4.00 mmol) and sodium iodide (1.20g, 8.00 mmol), and the reaction mixture was stirred at 100 C for 15 h. After cooling down to room temperature, magnesium powder (97 mg, 4.00 mmol) was added under argon, and the reaction mixture was stirred at room temperature for 36 h. The product was extracted by pentane (3 20 ml), and the volatiles were removed under vacuum, yielding an off white solid. Isolated yield: 507 mg, 64%. 31 P{ 1 H} NMR *Et 2O from C 6D 6 * Figure S2. 1 H NMR and 31 P{ 1 H} NMR spectra of 5b in C6D6 at RT measured on a 500 MHz Varian NMR spectrometer. S5

6 III. C-P Bond cleavage observation in Ph (PCP)H and ipr (PNP) synthesis The benzyl C-P bond cleavage was observed in the synthesis of Ph (PCP)H (5d) and ipr (PNP) (5e), which gave rise to the formation of (3-methylbenzyl)diphenylphosphine (5d ) and 2- ((diisopropylphosphanyl)methyl)-6-methylpyridine (5e ) as side products. The following two 1 H NMR spectra showed the identification of these side products. In the synthesis of 5d, two small peaks were observed at 3.24 ppm and 2.02 ppm (Figure S3), which corresponded to the benzylic protons and methyl protons of 5d. * * Figure S3. 1 H NMR spectrum of 5d and 5d in C6D6 at RT measured on a 500 MHz Varian NMR spectrometer. S6

7 Analogously, in the synthesis of 5e, two small peaks were observed at 2.99 ppm (d, JH-P = 1.5 Hz) and 2.40 ppm (s) (Figure S4), which corresponded to the benzylic protons and methyl protons of 5e. * * Figure S4. 1 H NMR spectrum of 5e and 5e in C6D6 at RT measured on a 500 MHz Varian NMR spectrometer. S7

8 IV. Control reactions related to the synthesis of ipr (PCP)NiX (6) Reaction of di-iso-propylchlorophosphine (2b-Cl) with nickel powder. In a screw cap culture tube, to the CD3CN solution (2 ml) of 2b-Cl (61 mg, 0.40 mmol) was added nickel powder (29 mg, 0.50 mmol). The reaction mixture was stirred at 100 C for 15 h. After cooling down to room temperature, the mixture was filtered through a pad of Celite. The filtrate was analyzed by 1 H NMR and 31 P NMR spectroscopy, showing only unreacted 2b-Cl was present. Reaction of xylylene dibromide (4a-Br2) with nickel powder. In a screw cap culture tube, to the CD3CN solution (2 ml) of 4a-Br2 (53 mg, 0.20 mmol) was added nickel powder (29 mg, 0.50 mmol). The reaction mixture was stirred at 100 C for 15 h. After cooling down to room temperature, the mixture was filtered through a pad of Celite. The filtrate was analyzed by 1 H NMR spectroscopy, showing 72% of unreacted 4a-Br2 along with new resonances attributable to compounds containing Ar-CH2CH2-Ar linkages from the likely benzyl-benzyl coupling (Figure S5). S8

9 * Δ Δ * * Δ Δ Figure S5. 1 H NMR spectrum of the mixture resulting after treatment of 4a-Br2, with Ni powder in CD3CN at 100 C for 15 h. The spectrum was measured at ambient temperature on a 500 MHz Varian NMR spectrometer. Signals corresponding to 4a-Br2 (72% unreacted) and to tentatively assigned products highlighted. S9

10 V. NMR spectra. isomer * Figure S6. 1 H NMR spectrum of 3a-BrCl in CD3CN at RT measured on a 500 MHz Varian NMR Spectrometer. S10

11 Figure S7. 13 C NMR spectrum of 3a-BrCl in CD3CN at RT measured on a 500 MHz Varian NMR Spectrometer. S11

12 Figure S8. 1 H NMR spectrum of 3b-BrCl in CD3CN at RT measured on a 500 MHz Varian NMR Spectrometer. S12

13 Figure S9. 13 C NMR spectrum of 3b-BrCl in CD3CN at RT measured on a 500 MHz Varian NMR Spectrometer. S13

14 Figure S10. 1 H NMR spectrum of 3a in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S14

15 Figure S C NMR spectrum of 3a in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S15

16 Figure S12. 1 H NMR spectrum of 3b in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S16

17 Figure S C NMR spectrum of 3b in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S17

18 Figure S14. 1 H NMR spectrum of 5a in C6D6 at RT measured on a 300 MHz Varian NMR Spectrometer. S18

19 Figure S C NMR spectrum of 5a in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S19

20 Figure S16. 1 H NMR spectrum of 5b in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S20

21 Figure S C NMR spectrum of 5b in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S21

22 Figure S18. 1 H NMR spectrum of 5c in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S22

23 Figure S C NMR spectrum of 5c in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S23

24 *Et 2O from C 6D 6 * * Figure S20. 1 H NMR spectrum of 5d in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S24

25 Figure S C NMR spectrum of 5d in C6D6 at RT measured on a 500 MHz Varian NMR Spectrometer. S25

26 *5e * * Figure S22. 1 H NMR spectrum of 5e in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S26

27 Figure S C NMR spectrum of 5e in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S27

28 * 6-Br * 6-Cl Figure S P NMR spectrum of mixture of 6-Cl and 6-Br in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S28

29 Figure S P NMR spectrum of 6-Br in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S29

30 Figure S26. 1 H NMR spectrum of 6-Br in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S30

31 Figure S C NMR spectrum of 6-Br in CD2Cl2 at RT measured on a 500 MHz Varian NMR Spectrometer. S31

32 *residual Et 2O, CH 2Cl 2 and pentane solvents * * * * Figure S28. 1 H NMR spectrum of 7 in CD3CN at RT measured on a 500 MHz Varian NMR Spectrometer. S32

33 Figure S29. 1 H NMR spectrum of 7 in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S33

34 Figure S C NMR spectrum of 7 in CDCl3 at RT measured on a 500 MHz Varian NMR Spectrometer. S34

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

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

Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.

Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W. Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes

More information

Supporting Information

Supporting Information Supporting Information Frustrated Lewis Pair-Like Splitting of Aromatic C-H bonds and Abstraction of Halogen Atoms by a Cationic [( F PNP)Pt] + Species Jessica C. DeMott, Nattamai Bhuvanesh and Oleg V.

More information

Supporting Information

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

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

Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes

Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes SUPPORTING INFORMATION Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes Alba Collado, Adrián Gómez-Suárez, Anthony R. Martin, Alexandra M. Z. Slawin, and

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. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes

Supporting Information. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes Supporting Information for Synthetic routes to [Au(HC)(OH)] (HC = - heterocyclic carbene) complexes Adrián Gómez-Suárez, Rubén S, Alexandra M. Z. Slawin and Steven P. olan* EaStChem School of chemistry,

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany SUPPRTIG MATERIAL Base Dependence in Copper-catalyzed Huisgen Reactions: Efficient Formation of Bistriazoles Yu Angell and Kevin Burgess *

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 Wiley-VCH 2007 69451 Weinheim, Germany Carbene Activation of P 4 and Subsequent Derivatization Jason D. Masuda, Wolfgang W. Schoeller, Bruno Donnadieu, and Guy Bertrand * [*] Dr.

More information

Supplementary Materials for

Supplementary Materials for www.advances.sciencemag.org/cgi/content/full/1/5/e1500304/dc1 Supplementary Materials for Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne click reaction This PDF file includes:

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

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Early-Late Heterobimetallic Rh-Ti and Rh-Zr Complexes via Addition of Early Metal Chlorides to Mono- and Divalent Rhodium Dan A. Smith and Oleg V. Ozerov* Department

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

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

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

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

Efficient Magnesium Catalysts for the Copolymerization of Epoxides and CO 2 ; Using Water to Synthesize Polycarbonate Polyols

Efficient Magnesium Catalysts for the Copolymerization of Epoxides and CO 2 ; Using Water to Synthesize Polycarbonate Polyols Supporting Information for Efficient Magnesium Catalysts for the Copolymerization of Epoxides and CO 2 ; Using Water to Synthesize Polycarbonate Polyols Michael R. Kember, Charlotte K. Williams* Department

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

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:

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

Supporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra

Supporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität

More information

Supporting Information

Supporting Information -S1- of 18 Functional Group Chemistry at the Group 4 Bent Metallocene Frameworks: Formation and Metal-free Catalytic Hydrogenation of Bis(imino-Cp)zirconium Complexes Kirill V. Axenov, Gerald Kehr, Roland

More information

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

Supporting Online Material

Supporting Online Material Supporting Online Material Topology Guided Design and Syntheses of Highly Stable Mesoporous Porphyrinic Zirconium MOFs with High Surface Area. Tian-Fu Liu, a Dawei Feng, a Ying-Pin Chen, a,b Lanfang Zou,

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

A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst

A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst Supplementary Information for A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst Rita Annunziata, Maurizio Benaglia, Mauro Cinquini,

More information

SUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles

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

More information

Supplementary Information

Supplementary Information Supplementary Information NE Difference Spectroscopy: SnPh 3 CH (b) Me (b) C()CH (a) Me (a) C()N Me (d) Me (c) Irradiated signal Enhanced signal(s) (%) Me (a) Me (c) 0.5, Me (d) 0.6 Me (b) - Me (c) H (a)

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

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

Iron Catalyzed Cross Couplings of Azetidines: Application to an Improved Formal Synthesis of a Pharmacologically Active Molecule

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

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

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

Supporting Information

Supporting Information Supporting Information Tris(allyl)indium Compounds: Synthesis and Structural Characterization Ilja Peckermann, Gerhard Raabe, Thomas P. Spaniol and Jun Okuda* Synthesis and characterization Figure S1:

More information

Supporting Information

Supporting Information Supporting Information Z-Selective Homodimerization of Terminal Olefins with a Ruthenium Metathesis Catalyst Benjamin K. Keitz, Koji Endo, Myles B. Herbert, Robert H. Grubbs* Arnold and Mabel Beckman Laboratories

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

Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes. Supporting Information

Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes. Supporting Information Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes Olga Ekkert, Gerald Kehr, Roland Fröhlich and Gerhard Erker Supporting Information Experimental Section

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

Electronic Supplementary Information

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

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation

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

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond

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

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

Introduction 1. DSC scan 5-bromo-2-aminopyridine..3. DSC scan 5-bromo-2-nitropyridine...4

Introduction 1. DSC scan 5-bromo-2-aminopyridine..3. DSC scan 5-bromo-2-nitropyridine...4 SUPPORTING INFORMATION Introduction 1 DSC scan 5-bromo-2-aminopyridine..3 DSC scan 5-bromo-2-nitropyridine.....4 Oxidant mixture. Adiabatic test stability, glass cell and Hastelloy C22 test cell 5 Hastelloy

More information

Activation of a hydroamination gold catalyst by oxidation of a redox non-innocent chlorostibine Z-ligand

Activation of a hydroamination gold catalyst by oxidation of a redox non-innocent chlorostibine Z-ligand Activation of a hydroamination gold catalyst by oxidation of a redox non-innocent chlorostibine Z-ligand Haifeng Yang and François P. Gabbaï Department of Chemistry, Texas A&M University, College Station,

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 for

Supporting Information for Supporting Information for Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis Koji Endo and Robert H. Grubbs* Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry

More information

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. 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

More information

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs) Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

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,

More information

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis

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

More information

Supporting Information for: Regioselective Electrophilic Borylation of Haloarenes.

Supporting Information for: Regioselective Electrophilic Borylation of Haloarenes. Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information for: Regioselective Electrophilic Borylation of Haloarenes. Alessandro Del

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

Supporting Information

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

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones related to proisocrinins Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,

More information

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,

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

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

Electronic supporting information for

Electronic supporting information for Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic supporting information for The effects of an ionic liquid on

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 Borata-alkene Derivatives Conveniently Made by Frustrated Lewis Pair Chemistry

Supporting Information Borata-alkene Derivatives Conveniently Made by Frustrated Lewis Pair Chemistry Supporting Information Borata-alkene Derivatives Conveniently Made by Frustrated Lewis Pair Chemistry Juri Möbus 1, Gerald Kehr, Constantin G. Daniliuc $, Roland Fröhlich $, Gerhard Erker* General Procedures.

More information

Supplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni

Supplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni Supplementary Figure 1 IR Spectroscopy. IR spectra of 1Cu and 1Ni as well as of the starting compounds, recorded as KBr-pellets on a Bruker Alpha FTIR spectrometer. Supplementary Figure 2 UV/Vis Spectroscopy.

More information

Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis

Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Fei Yu, Matthew S. McConnell, and Hien M. Nguyen* Department of Chemistry, University of Iowa, Iowa

More information

Supporting Information For:

Supporting Information For: Supporting Information For: Highly Fluorinated Ir(III)- 2,2 :6,2 -Terpyridine -Phenylpyridine-X Complexes via Selective C-F Activation: Robust Photocatalysts for Solar Fuel Generation and Photoredox Catalysis

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

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

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

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

Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene

Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene Antoine Buchard, Audrey Auffrant, Christian Klemps, Laurence Vu-Do, Leïla Boubekeur, Xavier F. Le Goff and Pascal Le Floch* Laboratoire

More information

Cationic Alkylaluminum-Complexed Zirconocene Hydrides as Participants in Olefin-Polymerization Catalysis. Supporting Information

Cationic Alkylaluminum-Complexed Zirconocene Hydrides as Participants in Olefin-Polymerization Catalysis. Supporting Information Cationic Alkylaluminum-Complexed Zirconocene Hydrides as Participants in Olefin-Polymerization Catalysis Steven M. Baldwin, John E. Bercaw, *, and Hans H. Brintzinger*, Contribution from the Arnold and

More information

Functionalization of the Aryl Moiety in the Pincer Complex. (NCN)Ni III Br 2 :

Functionalization of the Aryl Moiety in the Pincer Complex. (NCN)Ni III Br 2 : Electronic Supporting Information For : Functionalization of the Aryl Moiety in the Pincer Complex (NCN)Ni III Br 2 : Insights on Ni III -Promoted Carbon-Heteroatom Coupling Jean-Philippe Cloutier and

More information

Supporting Information

Supporting Information Discovery of rganic Halides as Regio-Switching xidants Supporting Information Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of rganic Halides as Regio-Switching

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

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

More information

Supplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

Supplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons Supplementary Material Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons İrfan Çapan a and Süleyman Servi b a Gazi University, Technical Sciences

More information

Pd(II) Catalyzed C3-selective arylation of pyridine with (hetero)arenes SUPPORTING INFORMATION

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

More information

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

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,

More information

Supporting Information

Supporting Information Supporting Information The Triple-Bond Metathesis of Aryldiazonium Salts: A Prospect for Dinitrogen Cleavage Aaron D. Lackner and Alois Fürstner* anie_201506546_sm_miscellaneous_information.pdf CRYSTALLOGRAPHIC

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

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks Mintu Porel and Christopher A. Alabi* School of Chemical and Biomolecular Engineering, Cornell University, Ithaca, New York 14853,

More information

Supporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives

Supporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives 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 2018 Supporting Information Application

More information

Supporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer

Supporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer Supporting Information for Polybenzimidazolium Salts: A ew Class of Anion-Conducting Polymer Owen D. Thomas, Kristen J. W. Y. Soo, Timothy J. Peckham, Mahesh P. Kulkarni and Steven Holdcroft* Department

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Simultaneous Production of p-tolualdehyde and Hydrogen Peroxide in Photocatalytic Oxygenation of p-xylene and Reduction of Oxygen with 9-Mesityl-1-Methylacridinium

More information

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are

More information

Supporting Information

Supporting Information 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

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Iridium-Catalyzed Dehydrocoupling of Primary Amine-Borane Adducts: A Route to High Molecular Weight Polyaminoboranes, Boron-Nitrogen Analogues

More information

Anion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle

Anion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information: Anion recognition in water by a rotaxane containing a secondary rim

More information

Supporting Information

Supporting Information Supporting Information Lewis acid-catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates Vincent Tran and Thomas G. Minehan * Department of Chemistry and

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Iodine Catalyzed xidation of Alcohols and Aldehydes to Carboxylic

More information

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters

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

More information

Chiral Sila[1]ferrocenophanes

Chiral Sila[1]ferrocenophanes Supporting Information Thermal Ring-Opening Polymerization of Planar- Chiral Sila[1]ferrocenophanes Elaheh Khozeimeh Sarbisheh, Jose Esteban Flores, Brady Anderson, Jianfeng Zhu, # and Jens Müller*, Department

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

Decisive Ligand Metathesis Effects in Au/Pd Bimetallic Catalysis

Decisive Ligand Metathesis Effects in Au/Pd Bimetallic Catalysis Supplementary information to: Decisive Ligand Metathesis Effects in Au/Pd Bimetallic Catalysis Juan delpozo, Juan A. Casares * and Pablo Espinet * Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias.

More information

Supporting Information

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

More information

Bulletin of the Chemical Society of Japan

Bulletin of the Chemical Society of Japan Supporting Information Bulletin of the Chemical Society of Japan Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives Kenjiro Kawamura,

More information

Supporting Information

Supporting Information Supporting Information Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp 2 ) H Functionalization Ashok Kumar Pandey, a Sang Hoon Han, a Neeraj Kumar Mishra,

More information

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 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

More information