Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage

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.

Automated summary

The study demonstrates that the reaction of arylthianthrenium salts with diarylphosphines can undergo phosphination via the cleavage of either an endocyclic or exocyclic C-S bond, with significantly higher speed in the presence of a palladacycle catalyst.