Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonatediesters with benzyl halides. Synthetic and mechanistic studies†‡§
Gaston Lavén,Marcin Kalek,Martina Jezowska
New Journal of Chemistry Pub Date : 02/12/2010 00:00:00 , DOI:10.1039/B9NJ00585D
Abstract

We have developed a new, efficient method for the synthesis of benzylphosphonate and benzylphosphonothioate diesters via a palladium(0)-catalyzed cross-coupling reaction between benzyl halides and H-phosphonate or H-phosphonothioate diesters, using Pd2(dba)3(CHCl3) as a palladium source and Xantphos as a supporting ligand. Some mechanistic aspects of these reactions were investigated using 31P NMR spectroscopy.

Graphical abstract: Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies