Literature DB >> 32579845

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

Michael F Wisthoff1, Sarah B Pawley1, Andrew P Cinderella1, Donald A Watson1.   

Abstract

We report a palladium-catalyzed, three-component carbosilylation reaction of internal symmetrical alkynes, silicon electrophiles, and primary alkyl zinc iodides. Depending on the choice of ligand, stereoselective synthesis of either cis- or trans-tetrasubstituted vinyl silanes is possible. We also demonstrate conditions for the Hiyama cross-coupling of these products to prepare geometrically defined tetrasubstituted alkenes.

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Year:  2020        PMID： 32579845      PMCID： PMC7405989          DOI： 10.1021/jacs.0c05382

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


  17 in total

1.  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

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

3.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

4.  Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions.

Authors:  James C Anderson; Rachel H Munday
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

5.  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

6.  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

7.  Direct Silyl-Heck Reaction of Chlorosilanes.

Authors:  Kazuhiro Matsumoto; Jiadi Huang; Yuki Naganawa; Haiqing Guo; Teruo Beppu; Kazuhiko Sato; Shigeru Shimada; Yumiko Nakajima
Journal:  Org Lett       Date:  2018-04-04       Impact factor: 6.005

8.  Heck-like Reactions Involving Heteroatomic Electrophiles.

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

9.  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

10.  Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins.

Authors:  Kenichiro Itami; Toshiyuki Kamei; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419
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  3 in total

1.  Bis-silylation of internal alkynes enabled by Ni(0) catalysis.

Authors:  Yun Zhang; Xi-Chao Wang; Cheng-Wei Ju; Dongbing Zhao
Journal:  Nat Commun       Date:  2021-01-04       Impact factor: 14.919

2.  Theoretical investigation on the effect of the ligand on bis-silylation of C(sp)-C(sp) by Ni complexes.

Authors:  Li Hui; He Yuhan; Wang Jiaqi
Journal:  RSC Adv       Date:  2022-01-05       Impact factor: 3.361

Review 3.  Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications.

Authors:  Rida Noor; Ameer Fawad Zahoor; Muhammad Irfan; Syed Makhdoom Hussain; Sajjad Ahmad; Ali Irfan; Katarzyna Kotwica-Mojzych; Mariusz Mojzych
Journal:  Molecules       Date:  2022-09-02       Impact factor: 4.927
  3 in total

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