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Electrochemical Difunctionalization of Alkenes by a Four‐Component Reaction Cascade Mumm Rearrangement: Rapid Access to Functionalized Imides
Author(s) -
Zhang Xiaofeng,
Cui Ting,
Zhao Xin,
Liu Ping,
Sun Peipei
Publication year - 2020
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.201913332
Subject(s) - chemistry , aryl , acetonitrile , electrochemistry , alcohol , hydrolysis , combinatorial chemistry , cascade , cascade reaction , organic chemistry , imide , catalysis , alkyl , electrode , chromatography
An electrochemical four‐component reaction cascade Mumm rearrangement was developed. It is a rare example of in situ generation of O‐acyl isoamides for 1,3‐(O→N) acyl transfer. Inexpensive, commercially available arylethylenes, aryl or heterocyclic acids, acetonitrile, and alcohols were used as substrates. A wide range of aryl acids and alcohols were tolerated and provided imides in satisfactory yields. Subsequent hydrolysis of imides could be utilized to synthesize valuable amides and β‐amino alcohol derivatives.