Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles

Org Lett. 2018 Nov 2;20(21):6746-6749. doi: 10.1021/acs.orglett.8b02854. Epub 2018 Oct 15.

Abstract

A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.

Publication types

  • Research Support, Non-U.S. Gov't