Base-Mediated Defluorosilylation of C(sp2 )-F and C(sp3 )-F Bonds

Angew Chem Int Ed Engl. 2019 Feb 11;58(7):2064-2068. doi: 10.1002/anie.201813294. Epub 2019 Jan 17.

Abstract

The ability to selectively forge C-heteroatom bonds by C-F scission is typically accomplished by metal catalysts, specialized ligands and/or harsh reaction conditions. Described herein is a base-mediated defluorosilylation of unactivated C(sp2 )-F and C(sp3 )-F bonds that obviates the need for metal catalysts. This protocol is characterized by its simplicity, mild reaction conditions, and wide scope, even within the context of late-stage functionalization, constituting a complementary approach to existing C-Si bond-forming protocols.

Keywords: cross-coupling; fluorine; reaction mechanisms; silylation; synthetic methods.