Nickel/photoredox-catalyzed carbonylative transformations of α-phosphorus-, α-sulfur-, and α-boron-substituted alkyl halides

Abstract

Organophosphorus compounds are important motifs in living organisms, medicinal chemistry, agricultural chemistry, materials science, catalysts, ligands, etc. However, catalytic carbonylative transformation of α-phosphorus, α-sulfur or α-boron substituted alkyl halides remains a formidable challenge due to α-heteroatom effects. In this report, we describe a nickel/photoredox dual-catalytic strategy for the direct amino- and alkoxycarbonylation of α-phosphorus, α-sulfur, and α-boron substituted organohalides with an array of reaction partners under low CO gas pressure which furnished various high-value products in excellent yields. The utility of this process was also demonstrated by the development of a new α-phosphine amide ligand. Additionally, this synergistic protocol also facilitates a sequential four-component carbonylation in the presence of vinyl phosphonate.