Diverse C–P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C–S Bond Cleavage
Yun Ye, Jie Zhu, Yinhua Huang
Abstract
Diverse C-P cross-couplings of arylthianthrenium salts with diarylphosphines producing various triarylphosphines via highly selective C-S bond cleavage are reported. In the absence of catalyst, the reaction of arylthianthrenium salts with diarylphosphines undergoes phosphinative ring opening exclusively via the cleavage of an endocyclic C-S bond of a thianthrene skeleton. The use of a palladacycle catalyst under otherwise the same conditions enables the phosphination via the cleavage of an exocyclic C-S bond with significantly higher speed.
Topics & Concepts
ChemistryCleavage (geology)Bond cleavageCatalysisStereochemistryRing (chemistry)Medicinal chemistryOrganic chemistryFracture (geology)Geotechnical engineeringEngineeringSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods