Literature DB >> 34570474

Cobalt-Catalyzed Enantiospecific Dynamic Kinetic Cross-Electrophile Vinylation of Allylic Alcohols with Vinyl Triflates.

Wei-Yuan Ma1, Guan-Yu Han1, Shaolin Kang1, Xiaobo Pang1, Xue-Yuan Liu1, Xing-Zhong Shu1.   

Abstract

Asymmetric cross-electrophile coupling has emerged as a promising tool for producing chiral molecules; however, the potential of this chemistry with metals other than nickel remains unknown. Herein, we report a cobalt-catalyzed enantiospecific vinylation reaction of allylic alcohol with vinyl triflates. This work establishes a new method for the synthesis of enantioenriched 1,4-dienes. The reaction proceeds through a dynamic kinetic coupling approach, which not only allows for direct functionalization of allylic alcohols but also is essential to achieve high chemoselectivity. The use of cobalt enables the reactions to proceed with high enantiospecificity, which have failed to be realized by nickel catalysts.

Entities:  

Year:  2021        PMID: 34570474     DOI: 10.1021/jacs.1c08695

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


  5 in total

1.  In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides.

Authors:  Benjamin K Chi; Jonas K Widness; Michael M Gilbert; Daniel C Salgueiro; Kevin J Garcia; Daniel J Weix
Journal:  ACS Catal       Date:  2021-12-21       Impact factor: 13.084

2.  Catalytic Enantioselective Hydrovinylation of Trialkylsilyloxy and Acetoxy-1,3-Dienes: Cationic Co(I) Complexes for the Synthesis of Chiral Enolate Surrogates and Their Applications for Synthesis of Ketones and Cross-Coupling Reagents in High Enantiomeric Purity.

Authors:  Souvagya Biswas; Kendra R Dewese; Balaram Raya; T V RajanBabu
Journal:  ACS Catal       Date:  2022-04-14       Impact factor: 13.700

3.  Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene.

Authors:  Yang Ye; Xiang Qi; Bing Xu; Ying Lin; Huan Xiang; Liang Zou; Xiang-Yang Ye; Tian Xie
Journal:  Chem Sci       Date:  2022-05-12       Impact factor: 9.969

4.  Decoding Key Transient Inter-Catalyst Interactions in a Reductive Metallaphotoredox-Catalyzed Allylation Reaction.

Authors:  Bart Limburg; Àlex Cristòfol; Arjan W Kleij
Journal:  J Am Chem Soc       Date:  2022-06-08       Impact factor: 16.383

5.  Oxyfunctionalization of Benzylic C-H Bonds of Toluene Mediated by Covalently Anchored Co-Schiff Bases.

Authors:  Guojun Shi; Yuxin Liang; Hongyu Zhou; Zhengliang Zhao; Wenjie Yang
Journal:  Molecules       Date:  2022-08-19       Impact factor: 4.927

  5 in total

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