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Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3 )-H Bonds.

ABSTRACT: Direct amination of C(sp3 )-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(sp3 )-H/N-H coupling that exhibits good reactivity with both sp2 and sp3 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.

SUBMITTER: Wang F

PROVIDER: S-EPMC6482061 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3 )-H Bonds.

Wang Fei F Wang Fei F Stahl Shannon S SS

Angewandte Chemie (International ed. in English) 20190314 19

Direct amination of C(sp3 )-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(sp3 )-H/N-H coupling that exhibits good reactivity with both sp2 and sp3 N-H bonds. The results show how use of iodide as an electrochemical mediator, in combination with ...[more]

PMID: 30763466

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