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Paired Electrosynthesis of Diacid and Diol Precursors Using Dienes and CO 2 as the Carbon Source
Author(s) -
Matthessen Roman,
Fransaer Jan,
Binnemans Koen,
De Vos Dirk E.
Publication year - 2015
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201402299
Subject(s) - electrosynthesis , carboxylation , conjugated system , chemistry , diol , electrochemistry , anode , reactivity (psychology) , double bond , alkyl , organic chemistry , carbon fibers , combinatorial chemistry , catalysis , polymer , materials science , electrode , medicine , alternative medicine , pathology , composite material , composite number
A new electrochemical methodology was devised and optimized, allowing a net incorporation of carbon dioxide in conjugated dienes in a one‐compartment cell using a non‐sacrificial anode. This divergent paired electrosynthesis of diacid and diol precursors was achieved through simultaneous cathodic carboxylation and anodic acetoxylation of conjugated dienes. After optimization of the reaction conditions, 1,3‐cyclohexadiene was converted to its corresponding 1,4‐dicarboxylate salt and 1,4‐diacetate ester with high yields and current efficiencies. A large effect of alkyl substitution and molecular configuration on the reactivity of conjugated double bonds towards carboxylation and acetoxylation was observed.