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Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
Author(s) -
You Cai,
Studer Armido
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007541
Subject(s) - chemistry , functional group , substrate (aquarium) , scope (computer science) , combinatorial chemistry , stereochemistry , organic chemistry , computer science , biology , programming language , ecology , polymer
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 2 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.