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Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids
Author(s) -
Wei BangYi,
Xie DongTai,
Lai ShengQiang,
Jiang Yu,
Fu Hong,
Wei Dian,
Han Bing
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.202012209
Subject(s) - chemistry , hydroxamic acid , annulation , stereoselectivity , electrosynthesis , regioselectivity , combinatorial chemistry , moiety , substrate (aquarium) , electrochemistry , organic chemistry , selectivity , anode , catalysis , electrode , oceanography , geology
This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode‐selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material‐tuned product selectivity.