Litcius/Paper detail

Photoinduced Homolysis of the Ni–P Bond via Ligand to Metal Charge Transfer for C–P Bond Formation in Nickel Catalysis

Yunpeng Ma, Hang Luo, Luqing Lin

2023Organic Letters16 citationsDOI

Abstract

Photoinduced homolysis of Ni II –carbon and −heteroatom bonds has been well studied for carbon–heteroatom couplings, but homolysis of the Ni II –P bond is still undisclosed. Herein, we describe the homolysis of Ni II –P bonds via ligand to metal charge transfer to access active nickel(I) complexes and phosphorus-centered radicals under visible-light irradiation for C–P couplings of diaryl phosphine oxides with aryl bromides. Experimental studies demonstrated that visible light enabled homolysis of the Ni II –P bond and the Ni I /Ni III self-sustained cycle was involved in C–P bond formation. Furthermore, homolysis of the Ni II –P bond can be applied to the hydrophosphination of [1.1.1]propellane in single-nickel photocatalysis.

Topics & Concepts

HomolysisChemistryPhotochemistryLigand (biochemistry)NickelPhosphineArylRadicalHeteroatomCatalysisOrganic chemistryRing (chemistry)AlkylBiochemistryReceptorRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods