Synthesis of 1,3-Bis-(boryl)alkanes Through Boronic Ester Induced Consecutive Double 1,2-Migration

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2020 Jun 25

PMID 32579295

Citations 10

Authors

Cai You

Armido Studer

Affiliations

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Abstract

A general and efficient approach for the preparation of 1,3-bis-(boryl)alkanes is introduced. It is shown that readily generated vinylboron ate complexes react with commercially available ICH Bpin to valuable 1,3-bis-(boryl)alkanes. The introduced transformation, which is experimentally easy to conduct, shows broad substrate scope and high functional-group tolerance. Mechanistic studies reveal that the reaction does not proceed via radical intermediates. Instead, an unprecedented boronic ester induced sequential bis-1,2-migration cascade is suggested.

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