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Electrochemical Oxidative Carbon‐Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers
Author(s) -
Guan Zhipeng,
Zhu Shuxiang,
Wang Siyuan,
Wang Huamin,
Wang Siyuan,
Zhong Xingxing,
Bu Faxiang,
Cong Hengjiang,
Lei Aiwen
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.202011329
Subject(s) - chemistry , sulfide , electrochemistry , functional group , combinatorial chemistry , sulfur , derivatization , molecule , carbon fibers , carbon atom , organic chemistry , ring (chemistry) , materials science , polymer , high performance liquid chromatography , electrode , composite number , composite material
Ethers (C−O/S) are ubiquitously found in a wide array of functional molecules and natural products. Nonetheless, the synthesis of imino sulfide ethers, containing an N(sp 2 )=C(sp 2 )−O/S fragment, still remains a challenge because of its sensitivity to acid. Developed here in is an unprecedented electrochemical oxidative carbon‐atom difunctionalization of isocyanides, providing a series of novel multisubstituted imino sulfide ethers. Under metal‐free and external oxidant‐free conditions, isocyanides react smoothly with simple and readily available mercaptans and alcohols. Importantly, the procedure exhibited high stereoselectivities, excellent functional‐group tolerance, and good efficiency on large‐scale synthesis, as well as further derivatization of the products.