Literature DB >> 21208005

Copper-catalyzed highly regioselective silylcupration of terminal alkynes to form α-vinylsilanes.

Peng Wang1, Xue-Liang Yeo, Teck-Peng Loh.   

Abstract

A highly regioselective synthesis of branched vinylsilanes through silicon-copper additions to terminal alkynes catalyzed by copper(I) was developed using methanol as additive. The corresponding vinylsilanes were obtained with excellent branched to linear selectivity of up to 99/1 in good yields.

Entities:  

Year:  2011        PMID： 21208005     DOI： 10.1021/ja109464u

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


  7 in total

Review 1.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

Authors:  Bogdan Marciniec; Cezary Pietraszuk; Piotr Pawluć; Hieronim Maciejewski
Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

2.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

3.  Copper(II)-catalyzed silylation of activated alkynes in water: diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds.

Authors:  Joseph A Calderone; Webster L Santos
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-14       Impact factor: 15.336

4.  Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si.

Authors:  Hiroto Yoshida
Journal:  Chem Rec       Date:  2016-01-20       Impact factor: 6.771

5.  Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes.

Authors:  Zheng-Li Liu; Chao Yang; Qi-Yan Xue; Meng Zhao; Cui-Cui Shan; Yun-He Xu; Teck-Peng Loh
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-04       Impact factor: 15.336

6.  Sodium silylsilanolate as a precursor of silylcopper species.

Authors:  Hiroki Yamagishi; Kenshiro Hitoshio; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

7.  Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.

Authors:  Yang Gao; Sima Yazdani; Aaron Kendrick; Glen P Junor; Taeho Kang; Douglas B Grotjahn; Guy Bertrand; Rodolphe Jazzar; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-29       Impact factor: 16.823
  7 in total

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