Photoinduced Remote C(sp3)-H Phosphonylation of Amides

Angew Chem Int Ed Engl. 2024 Apr 3:e202400856. doi: 10.1002/anie.202400856. Online ahead of print.

Abstract

The present study reports an unprecedented protocol for the phosphonylation of unactivated C(sp3)-H bonds. By utilizing 1 mol % 4DPAIPN (1,2,3,5-tetrakis(diphenylamino)-4,6-dicyanobenzene) as the catalyst, satisfactory yields of γ-phosphonylated amides are obtained through a visible-light-induced reaction between N-((4-cyanobenzoyl)oxy)alkanamides and 9-fluorenyl o-phenylene phosphite at room temperature. This protocol demonstrates broad substrate scope and wide functional group compatibility.

Keywords: 1,5-HAT; C−H activation; energy transfer; phosphonylation; radicals.