Eight-Membered Palladacycle Intermediate Enabled Synthesis of Cyclic Biarylphosphonates

Chemistry. 2024 Jan 11;30(3):e202302416. doi: 10.1002/chem.202302416. Epub 2023 Nov 20.

Abstract

Transition-metal-catalyzed coupling reactions that involve the direct functionalization of insert C-H bond represent one of the most efficient strategies for forming carbon-carbon bonds. Herein, a palladium-catalyzed intramolecular C-H bond arylation of triaryl phosphates is reported to access seven-membered cyclic biarylphosphonate targets. The reaction is achieved via a unique eight-membered palladacyclic intermediate and shows good functional group compatibility. Meanwhile, the product can be readily converted into other valuable phosphate compounds.

Keywords: cross-coupling; cyclic biarylphosphonates; direct arylation; palladium-catalyzed.