Literature DB >> 24914247

The First Example of Nickel-Catalyzed Silyl-Heck Reactions: Direct Activation of Silyl Triflates Without Iodide Additives.

Jesse R McAtee1, Sara E S Martin1, Andrew P Cinderella1, William B Reid1, Keywan A Johnson1, Donald A Watson1.   

Abstract

For the first time, nickel-catalyzed silyl-Heck reactions are reported. Using simple phosphine-supported nickel catalysts, direct activation of silyl triflates has been achieved. These results contrast earlier palladium-catalyzed systems, which require iodide additives to activate silyl-triflates. These nickel-based catalysts exhibit good functional group tolerance in the preparation of vinyl silanes, and unlike earlier systems, allows for the incorporation of trialkylsilanes larger than Me3Si.

Entities:  

Year:  2014        PMID: 24914247      PMCID: PMC4047519          DOI: 10.1016/j.tet.2014.03.021

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  12 in total

1.  Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds.

Authors:  Ian Fleming; Asuncion Barbero; David Walter
Journal:  Chem Rev       Date:  1997-10-01       Impact factor: 60.622

2.  Activation of "inert" alkenyl/aryl C-O bond and its application in cross-coupling reactions.

Authors:  Bi-Jie Li; Da-Gang Yu; Chang-Liang Sun; Zhang-Jie Shi
Journal:  Chemistry       Date:  2011-01-17       Impact factor: 5.236

Review 3.  Silicon-based cross-coupling reactions in the total synthesis of natural products.

Authors:  Scott E Denmark; Jack H-C Liu
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

4.  Facile strategy to well-defined water-soluble boronic acid (co)polymers.

Authors:  Jennifer N Cambre; Debashish Roy; Sudershan R Gondi; Brent S Sumerlin
Journal:  J Am Chem Soc       Date:  2007-08-04       Impact factor: 15.419

5.  Silicon-based cross-coupling reaction: an environmentally benign version.

Authors:  Yoshiaki Nakao; Tamejiro Hiyama
Journal:  Chem Soc Rev       Date:  2011-07-14       Impact factor: 54.564

6.  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

7.  Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

Authors:  Sze-Sze Ng; Chun-Yu Ho; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

8.  Palladium-catalysed cross-coupling of organosilicon reagents.

Authors:  Hannah F Sore; Warren R J D Galloway; David R Spring
Journal:  Chem Soc Rev       Date:  2011-11-02       Impact factor: 54.564

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.  The Kulinkovich reaction in the synthesis of constrained n,n-dialkyl neurotransmitter analogues.

Authors:  Catherine A Faler; Madeleine M Joullié
Journal:  Org Lett       Date:  2007-04-21       Impact factor: 6.005

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  14 in total

1.  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

2.  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 3.  Cross-Coupling of Heteroatomic Electrophiles.

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

4.  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

5.  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

6.  Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

Authors:  Jean-Nicolas Desrosiers; Jialin Wen; Sergei Tcyrulnikov; Soumik Biswas; Bo Qu; Liana Hie; Dmitry Kurouski; Ling Wu; Nelu Grinberg; Nizar Haddad; Carl A Busacca; Nathan K Yee; Jinhua J Song; Neil K Garg; Xumu Zhang; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

7.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

8.  Heck-like Reactions Involving Heteroatomic Electrophiles.

Authors:  Bojan Vulovic; Donald A Watson
Journal:  European J Org Chem       Date:  2017-07-05

9.  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

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

Authors:  Andrew P Cinderella; Bojan Vulovic; Donald A Watson
Journal:  J Am Chem Soc       Date:  2017-06-01       Impact factor: 15.419

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