Haloamines as Bifunctional Reagents for Oxidative Aminohalogenation of Maleimides

Org Lett. 2021 May 7;23(9):3669-3673. doi: 10.1021/acs.orglett.1c01052. Epub 2021 Apr 12.

Abstract

An unprecedented copper-catalyzed oxidative aminohalogenation of electron-deficient maleimides with secondary amines and NXS (X = Cl, Br, I) was developed, in which the N-X bonds generated in situ were used as difunctionalized reagents. The distinctive features of this multicomponent reaction include a simple green catalytic system, a spectral substrate range, and the late-stage modification of drug molecules. Most importantly, this umpolung radical cascade strategy exploits the in situ formation of N-iodoamines that enable efficient alkene aminoiodination.

Publication types

  • Research Support, Non-U.S. Gov't