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Dual Functionalization of α‐Monoboryl Carbanions through Deoxygenative Enolization with Carboxylic Acids
Author(s) -
Sun Wei,
Wang Lu,
Xia Chungu,
Liu Chao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801679
Subject(s) - carbanion , electrophile , chemistry , keto–enol tautomerism , surface modification , carboxylic acid , carboxylate , reagent , organic chemistry , catalysis
A dual functionalization of 1,1‐diborylalkanes through deoxygenative enolization with carboxylic acids was developed. 1,1‐Diborylalkanes were activated by MeLi to generate α‐monoboryl carbanions. In situ IR spectroscopy indicated an interaction between carboxylic acid and 1,1‐diborylalkane before addition of the activation reagent. Release of the active α‐monoboryl carbanion from the masked form was necessary for its reaction with carboxylate to afford enolate species. Electrophilic trapping of enolate species with various electrophiles achieved dual functionalization of 1,1‐diborylalkanes to afford a variety of α‐mono, di‐, and tri‐substituted ketones.