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Merging Photochemistry with Electrochemistry: Functional‐Group Tolerant Electrochemical Amination of C(sp 3 )−H Bonds
Author(s) -
Wang Fei,
Stahl Shan S.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813960
Subject(s) - amination , electrochemistry , chemistry , photochemistry , iodide , functional group , reactivity (psychology) , combinatorial chemistry , electrode , inorganic chemistry , organic chemistry , catalysis , medicine , polymer , alternative medicine , pathology
Abstract Direct amination of C(sp 3 )−H bonds is of broad interest in the realm of C−H functionalization because of the prevalence of nitrogen heterocycles and amines in pharmaceuticals and natural products. Reported here is a combined electrochemical/photochemical method for dehydrogenative C(sp 3 )−H/N−H coupling that exhibits good reactivity with both sp 2 and sp 3 N−H bonds. The results show how use of iodide as an electrochemical mediator, in combination with light‐induced cleavage of intermediate N−I bonds, enables the electrochemical process to proceed at low electrode potentials. This approach significantly improves the functional‐group compatibility of electrochemical C−H amination, for example, tolerating electron‐rich aromatic groups that undergo deleterious side reactions in the presence of high electrode potentials.