Asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by electrogenerated chiral [CoI(salen)]− complex

The feasibility of asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by the electrogenerated chiral [CoI(salen)]− complex has been investigated for the first time. Using this system, optically active 2-phenylpropionic acid in 37% yield and 83% ee is synthesized from 1-phenylethyl c...

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Bibliographic Details
Published in:Electrochemistry communications 2014-05, Vol.42, p.55-59
Main Authors: Chen, Bao-Li, Zhu, Hong-Wei, Xiao, Yan, Sun, Qi-Long, Wang, Huan, Lu, Jia-Xing
Format: Article
Language:English
Subjects:
1-Phenylethyl chloride
Asymmetry
Chemistry
chiral CoII(salen) complex
CO2
Electrocarboxylation
Electrochemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanism of reactions
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Summary:The feasibility of asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by the electrogenerated chiral [CoI(salen)]− complex has been investigated for the first time. Using this system, optically active 2-phenylpropionic acid in 37% yield and 83% ee is synthesized from 1-phenylethyl chloride and CO2. The electrochemical behavior of the catalyst and the optimization of synthesis conditions are discussed. This study provides a new procedure for the asymmetric synthesis of a chiral compound and expands the applications of chiral CoII(salen) in the electrochemical asymmetric fixation of CO2. [Display omitted] •Electrogenerated chiral [CoI(salen)]− achieves asymmetric electrocarboxylation of a racemic organic halide.•Application of chiral CoII(salen) in electrochemical asymmetric fixation of CO2 has been developed.•Applications of asymmetric synthesis by electrochemical methodology has been expanded.
ISSN:1388-2481
1873-1902
DOI:10.1016/j.elecom.2014.02.009