Literature DB >> 28570065

Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction.

Andrew P Cinderella1, Bojan Vulovic1, Donald A Watson1.   

Abstract

We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

Entities:  

Year:  2017        PMID： 28570065      PMCID： PMC5531279          DOI： 10.1021/jacs.7b04364

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  23 in total

1.  Organosilicon molecules with medicinal applications.

Authors:  Annaliese K Franz; Sean O Wilson
Journal:  J Med Chem       Date:  2012-11-06       Impact factor: 7.446

2.  Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: a silyl-Heck reaction.

Authors:  Jesse R McAtee; Sara E S Martin; Derek T Ahneman; Keywan A Johnson; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-01       Impact factor: 15.336

3.  Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Authors:  William B Reid; Jesse J Spillane; Sarah B Krause; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-04-22       Impact factor: 15.419

4.  Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

Authors:  Jesse R McAtee; Sarah B Krause; Donald A Watson
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

Review 5.  Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides.

Authors:  Emmanuelle Rémond; Charlotte Martin; Jean Martinez; Florine Cavelier
Journal:  Chem Rev       Date:  2016-08-16       Impact factor: 60.622

6.  Efficient and rapid C-Si bond cleavage in supercritical water.

Authors:  Kenichiro Itami; Koji Terakawa; Jun-Ichi Yoshida; Okitsugu Kajimoto
Journal:  J Am Chem Soc       Date:  2003-05-21       Impact factor: 15.419

7.  Diastereoconvergent Negishi cross-coupling using functionalized cyclohexylzinc reagents.

Authors:  Kohei Moriya; Paul Knochel
Journal:  Org Lett       Date:  2014-01-15       Impact factor: 6.005

Review 8.  pi-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II).

Authors:  Ian J S Fairlamb
Journal:  Org Biomol Chem       Date:  2008-09-09       Impact factor: 3.876

9.  Preparation of vinyl silyl ethers and disiloxanes via the silyl-Heck reaction of silyl ditriflates.

Authors:  Sara E S Martin; Donald A Watson
Journal:  J Am Chem Soc       Date:  2013-08-28       Impact factor: 15.419

10.  Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors:  Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
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  12 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Stereoselective Synthesis of Cis- and Trans-Tetrasubstituted Vinyl Silanes Using a Silyl-Heck Strategy and Hiyama Conditions for Their Cross-Coupling.

Authors:  Michael F Wisthoff; Sarah B Pawley; Andrew P Cinderella; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-06-30       Impact factor: 15.419

3.  Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

Authors:  William B Reid; Jesse R McAtee; Donald A Watson
Journal:  Organometallics       Date:  2019-09-26       Impact factor: 3.876

4.  Palladium-Catalyzed Cross-Coupling of Monochlorosilanes And Grignard Reagents.

Authors:  Bojan Vulovic; Andrew P Cinderella; Donald A Watson
Journal:  ACS Catal       Date:  2017-10-30       Impact factor: 13.084

5.  A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

Authors:  Sarah B Krause; Jesse R McAtee; Glenn P A Yap; Donald A Watson
Journal:  Org Lett       Date:  2017-09-29       Impact factor: 6.005

6.  Cobalt-catalyzed difluoroalkylation of tertiary aryl ketones for facile synthesis of quaternary alkyl difluorides.

Authors:  Chao Li; Yi-Xuan Cao; Rui Wang; Yi-Ning Wang; Quan Lan; Xi-Sheng Wang
Journal:  Nat Commun       Date:  2018-11-23       Impact factor: 14.919

7.  Catalyst-controlled regiodivergent ring-opening C(sp3)-Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis.

Authors:  Youhei Takeda; Kaoru Shibuta; Shohei Aoki; Norimitsu Tohnai; Satoshi Minakata
Journal:  Chem Sci       Date:  2019-07-31       Impact factor: 9.825

8.  Stereospecific and Chemoselective Copper-Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates.

Authors:  Jonas Scharfbier; Benjamin M Gross; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-04       Impact factor: 15.336

9.  Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes.

Authors:  Yangbin Liu; Daniele Fiorito; Clément Mazet
Journal:  Chem Sci       Date:  2018-05-23       Impact factor: 9.825

Review 10.  Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.

Authors:  Mario P Wiesenfeldt; Zackaria Nairoukh; Toryn Dalton; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-29       Impact factor: 15.336
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