Literature DB >> 29868244

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

Bojan Vulovic1, Andrew P Cinderella1, Donald A Watson1.   

Abstract

Using a palladium catalyst supported by DrewPhos, the alkylation of monochlorosilanes with primary and secondary alkyl-magnesium halides is now possible. Arylation with sterically demanding aromatic magnesium halides is also enabled. This transformation overcomes the high bond strength of the Si-Cl bond (113 kcal/mol) and is a rare example of a transition-metal catalyzed process involving its activation. Due to the availability of both chlorosilanes and organomagnesium halide reagents, this method allows for the preparation of a wide range of alkyl and aryl silanes.

Entities:  

Year:  2017        PMID: 29868244      PMCID: PMC5984048          DOI: 10.1021/acscatal.7b03465

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  42 in total

1.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

3.  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

4.  Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes.

Authors:  Manas Das; Donal F O'Shea
Journal:  J Org Chem       Date:  2014-06-03       Impact factor: 4.354

5.  Stereoselective Peterson olefinations from bench-stable reagents and N-phenyl imines.

Authors:  Manas Das; Atul Manvar; Maïwenn Jacolot; Marco Blangetti; Roderick C Jones; Donal F O'Shea
Journal:  Chemistry       Date:  2015-03-11       Impact factor: 5.236

6.  Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C-O Bond Activation.

Authors:  Mamoru Tobisu; Tsuyoshi Takahira; Toshifumi Morioka; Naoto Chatani
Journal:  J Am Chem Soc       Date:  2016-05-23       Impact factor: 15.419

7.  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

8.  Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors:  Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Cross-coupling reaction of alkyl halides with grignard reagents catalyzed by Ni, Pd, or Cu complexes with pi-carbon ligand(s).

Authors:  Jun Terao; Nobuaki Kambe
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

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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  7 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.  An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond.

Authors:  Lingxiang Lu; Juno C Siu; Yihuan Lai; Song Lin
Journal:  J Am Chem Soc       Date:  2020-12-08       Impact factor: 15.419

3.  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

4.  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

5.  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

6.  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

7.  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

  7 in total

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