Literature DB >> 23984876

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

Sara E S Martin1, Donald A Watson.   

Abstract

Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity.

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Year:  2013        PMID： 23984876      PMCID： PMC3816510          DOI： 10.1021/ja407748z

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


  16 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.  Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

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

Review 4.  Selected patented cross-coupling reaction technologies.

Authors:  Jean-Pierre Corbet; Gérard Mignani
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

5.  Iridium-catalyzed, diastereoselective dehydrogenative silylation of terminal alkenes with (TMSO)2MeSiH.

Authors:  Chen Cheng; Eric M Simmons; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-15       Impact factor: 15.336

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.  Sequential ring-closing metathesis and silicon-assisted cross-coupling reactions: stereocontrolled synthesis of highly substituted unsaturated alcohols.

Authors:  S E Denmark; S M Yang
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

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.  On-Surface Cross Coupling Methods for the Construction of Modified Electrode Assemblies with Tailored Morphologies.

Authors:  Amber A S Gietter; Rachel C Pupillo; Glenn P A Yap; Thomas P Beebe; Joel Rosenthal; Donald A Watson
Journal:  Chem Sci       Date:  2013-01-01       Impact factor: 9.825

10.  Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates.

Authors:  Scott E Denmark; Ramzi F Sweis
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005
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  19 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.  Manganese-catalysed divergent silylation of alkenes.

Authors:  Jie Dong; Xiang-Ai Yuan; Zhongfei Yan; Liying Mu; Junyang Ma; Chengjian Zhu; Jin Xie
Journal:  Nat Chem       Date:  2020-12-14       Impact factor: 24.427

5.  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

6.  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

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

Authors:  Jesse R McAtee; Sara E S Martin; Andrew P Cinderella; William B Reid; Keywan A Johnson; Donald A Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

9.  Heck-like Reactions Involving Heteroatomic Electrophiles.

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

10.  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
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