Work

Merging Photochemistry with Electrochemistry: Functional‐Group Tolerant Electrochemical Amination of C(sp 3 )−H Bonds

Year: 2019

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201813960

Authors: Fei Wang, Shannon S. Stahl

Institution: University of Wisconsin–Madison

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, National Institute of General Medical Sciences

Awards: G4381830148, Acquisition of a 400 MHz NMR Spectrometer for Chemical Research and Learning, QExactive (Orbitrap) mass spectrometer, G9000000692