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An Electrochemical Cinnamyl C—H Amination Reaction Using Carbonyl Sulfamate
Author(s) -
Liu Shuai,
Li Jin,
Wang Dalin,
Liu Feng,
Liu Xu,
Gao Yongyuan,
Jie Dai,
Cheng Xu
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900028
Subject(s) - chemistry , amination , chemoselectivity , electrochemistry , reductive amination , organic chemistry , nucleophile , amine gas treating , transition metal , sulfonyl , combinatorial chemistry , hydrolysis , catalysis , electrode , alkyl
Summary of main observation and conclusion An electrochemical cinnamyl C—H amination reaction in the absence of transition metal catalyst and oxidant was reported. The choice of carbonyl sulfamate as nitrogen source is the key to achieve desired chemoselectivity. A series of terminal amine derivatives are prepared using this protocol and the sulfonyl group can be removed with basic hydrolysis. The reaction is suggested to proceed via a continuous anodic oxidation, deprotonation, anodic oxidation, and intermolecular nucleophilic addition pathway, demonstrating the first example of electrochemical cinnamyl C—H amination.