Catalyst-free room-temperature decarboxylative tri- or tetrafunctionalization of alkynyl carboxylic acids with N-fluorobenzenesulfonimide (NFSI) and diselenides?

Green Chemistry Pub Date: 2018-01-02 DOI: 10.1039/C7GC03267F

Abstract

The combination of N-fluorobenzenesulfonimide (NFSI) with diselenides allowed the rapid decarboxylative tri- or tetrafunctionalization of alkynyl carboxylic acids under catalyst-free room-temperature conditions. This reaction offers a novel and facile route to polyseleno-substituted enamines, which employs NFSI not only as a useful oxidant but also as an efficient amination reagent, displays a broad substrate scope and results in good to excellent yields. An electrophilic mechanism is proposed for the transformation.

Graphical abstract: Catalyst-free room-temperature decarboxylative tri- or tetrafunctionalization of alkynyl carboxylic acids with N-fluorobenzenesulfonimide (NFSI) and diselenides
Recommended Literature