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Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2‐Dichloroethane
Author(s) -
Liang Yujie,
Lin Fengguirong,
Adeli Yeerlan,
Jin Rui,
Jiao Ning
Publication year - 2019
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.201814570
Subject(s) - dichloroethane , electrocatalyst , chemistry , reagent , bifunctional , vinyl chloride , aryl , catalysis , chloride , 1,2 dichloroethane , organic chemistry , combinatorial chemistry , copolymer , polymer , electrochemistry , electrode , alkyl
Although the application of 1,2‐dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C−H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value‐added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late‐stage chlorination of bioactive molecules.