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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 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.201813960
Subject(s) - amination , electrochemistry , chemistry , iodide , photochemistry , functional group , reactivity (psychology) , electrode , combinatorial chemistry , inorganic chemistry , organic chemistry , catalysis , medicine , polymer , alternative medicine , pathology
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.