Metal-Free Electrophilic Phosphination/Cyclization of Alkynes

J Am Chem Soc. 2017 May 3;139(17):6106-6109. doi: 10.1021/jacs.7b02977. Epub 2017 Apr 20.

Abstract

A metal-free electrophilic phosphination reaction has been developed. Electrophilic phosphorus species generated in situ from secondary phosphine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleophiles to afford the corresponding phosphinated cyclization products in good yield. Preliminary NMR studies show that phosphirenium species may be involved as intermediates of the cyclization reactions.

Publication types

  • Research Support, Non-U.S. Gov't