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CO 2 Conversion into Esters by Fluoride‐Mediated Carboxylation of Organosilanes and Halide Derivatives
Author(s) -
Frogneux Xavier,
von Wolff Niklas,
Thuéry Pierre,
Lefèvre Guillaume,
Cantat Thibault
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201505092
Subject(s) - carboxylation , electrophile , fluoride , chemistry , halide , catalysis , metal , polymer chemistry , organic chemistry , inorganic chemistry
A one‐step conversion of CO 2 into heteroaromatic esters is presented under metal‐free conditions. Using fluoride anions as promoters for the C−Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO 2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO 2 in the C−Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO 2 into a polyester material for the first time.