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Polyhalides as Efficient and Mild Oxidants for Oxidative Carbene Organocatalysis by Radical Processes
Author(s) -
Wu Xingxing,
Zhang Yuexia,
Wang Yuhuang,
Ke Jie,
Jeret Martin,
Reddi Rambabu N.,
Yang Song,
Song BaoAn,
Chi Yonggui Robin
Publication year - 2017
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.201611692
Subject(s) - carbene , organocatalysis , oxidative phosphorylation , chemistry , photochemistry , catalysis , organic chemistry , combinatorial chemistry , enantioselective synthesis , biochemistry
Simple and inexpensive polyhalides (CCl 4 and C 2 Cl 6 ) have been found to be effective and versatile oxidants in removing electrons from Breslow intermediates under N‐heterocyclic carbene (NHC) catalysis. This oxidative reaction involves multiple single‐electron‐transfer (SET) processes and several radical intermediates. The α, β, and γ‐carbon atoms of aldehydes and enals could be readily functionalized. Given the low cost of the oxidants and the broad applicability of the reactions, this study is expected to greatly enhance the feasibility of oxidative NHC catalysis for large‐scale applications. Also this new SET radical process with polyhalides as single‐electron oxidants will open a new avenue in the development of NHC‐catalyzed radical reactions.