Merging Photochemistry with Electrochemistry: Functional Group Tolerant Electrochemical Amination of sp³ C–H Bonds

Direct amination of sp³ C–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. Here, we report 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.

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