Photoinduced Copper-Catalyzed C(sp 3 )-P Bond Formation by Coupling of Secondary Phosphines with N-(Acyloxy)phthalimides and N-Fluorocarboxamides.

A photoinduced copper-catalyzed C(sp 3 )-P bond formation has been developed by using N-(acyloxy)phthalimides as radical precursors and secondary phosphine boranes as coupling partners. A variety of alkyl carboxylic acid derivatives can be readily transformed into the corresponding phosphines with high reaction efficiency and structural diversity. Besides, utilizing the 1,5-HAT of the N-centered radical process, the δ C(sp 3 )-H bond can be coupled with secondary phosphines, which provides a novel method for the regioselective formation of C(sp 3 )-P bonds.