Copper-Mediated C-H Amination of Imidazopyridines with N-Fluorobenzenesulfonimide

J Org Chem. 2018 Nov 16;83(22):13991-14000. doi: 10.1021/acs.joc.8b02348. Epub 2018 Nov 2.

Abstract

A copper-mediated direct C3 amination of imidazopyridines has been disclosed under additive-free conditions in short reaction times. This methodology utilizes commercially available N-fluorobenzenesulfonimide (NFSI) as the amino source, which exhibits broad substrate scope and good functional group tolerance. The obtained C3-aminated imidazopyridines can undergo further desulfonylation transformations. Control experiments suggest that this reaction probably proceeds via a free-radical mechanism. Moreover, NFSI also shows potential application in C-H fluorination of imidazopyridines.

Publication types

  • Research Support, Non-U.S. Gov't