DFT Analysis into the Calcium(II)-Catalyzed Coupling of Alcohols With Vinylboronic Acids: Cooperativity of Two Different Lewis Acids and Counterion Effects | Zendy

Shengwen Yang | Zendy; Christophe Bour | Zendy; David Lebœuf | Zendy; Vincent Gandon | Zendy

Open Access

DFT Analysis into the Calcium(II)-Catalyzed Coupling of Alcohols With Vinylboronic Acids: Cooperativity of Two Different Lewis Acids and Counterion Effects

Author(s) -

Shengwen Yang,

Christophe Bour,

David Lebœuf,

Vincent Gandon

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c01263

Subject(s) - chemistry , lewis acids and bases , counterion , cooperativity , steric effects , catalysis , calcium , density functional theory , computational chemistry , organic chemistry , ion , biochemistry

The mechanism of the calcium-catalyzed coupling of alcohols with vinylboronic acids has been analyzed by means of density functional theory computations. This study reveals that the calcium and boron Lewis acids associate to form a superelectrophile able to promote a pericyclic group transfer reaction with allyl alcohols. With other alcohols, the two Lewis acids act synergistically to activate the OH functionality and trigger a S N i reaction pathway. These two mechanisms are affected by the nature of the counterions, which has been rationalized by electronic and steric factors.

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