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Selective Electrosynthetic Hydrocarboxylation of α,β‐Unsaturated Esters with Carbon Dioxide **
Author(s) -
Sheta Ahmed M.,
Alkayal Anas,
Mashaly Mohammad A.,
Said Samy B.,
Elmorsy Saad S.,
Malkov Andrei V.,
Buckley Benjamin R.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105490
Subject(s) - carboxylation , chemistry , regioselectivity , reagent , organic chemistry , amine gas treating , olefin fiber , carbon monoxide , hydroformylation , selectivity , carboxylic acid , carboxylate , catalysis , combinatorial chemistry , rhodium
The carboxylation of low‐value commodity chemicals to provide higher‐value carboxylic acids is of significant interest. Recently alternative routes to the traditional hydroformylation processes that used potentially toxic carbon monoxide and a transition metal catalyst have appeared. A significant challenge has been the selectivity observed for olefin carboxylation. Photochemical methods have shown a viable route towards the hydrocarboxylation of α,β‐unsaturated alkenes but rely on the use of an excess reducing or amine reagent. Herein we report our investigations of an electrochemical approach that is able to hydrocarboxylate α,β‐unsaturated alkenes with excellent regioselectivity and the ability to carboxylate hindered substrates to afford α‐quaternary center carboxylic acids. The reported process requires no chromatography and the products are purified by simple crystallization from the reaction mixture after work‐up.