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Boosting the Catalytic Performance of Organic Salts for the Fast and Selective Synthesis of α‐Alkylidene Cyclic Carbonates from Carbon Dioxide and Propargylic Alcohols
Author(s) -
Grignard Bruno,
Ngassamtounzoua Charlène,
Gennen Sandro,
Gilbert Bernard,
Méreau Raphaël,
Jerome Christine,
Tassaing Thierry,
Detrembleur Christophe
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800063
Subject(s) - catalysis , selectivity , chemistry , alcohol , organic synthesis , oxalate , solvent , organic chemistry , combinatorial chemistry
The synthesis of α‐alkylidene cyclic carbonates (αCCs) by the carboxylative coupling of CO 2 with propargylic alcohols is receiving increasing interest but requires the use of catalysts that are most often added in large quantities and/or lack selectivity. Herein, we describe the fine‐tuning of the structure of organocatalysts of the ammonium‐type that enables us to identify the important structural parameters that dictate their catalytic performance. Tetrabutylammonium oxalate was revealed to be one of the most attractive organocatalysts with a remarkably fast, complete and selective production of αCCs at a low catalyst loading (2.5 mol %) under solvent‐free conditions. This study opens new avenues for the facile and selective synthesis of libraries of αCCs from CO 2 and propargylic alcohol by using simple organocatalysts.