Double Hydrophosphorylation of Nitriles Catalyzed by Rare-Earth-Metal Lanthanum

J Org Chem. 2020 Nov 20;85(22):14720-14729. doi: 10.1021/acs.joc.0c02016. Epub 2020 Oct 30.

Abstract

A high-yielding and atom-efficient protocol for the double hydrophosphorylation of nitriles using a lanthanum-based N,N-dimethylbenzylamine complex (La(DMBA)3) as a precatalyst is reported. This method provides a straightforward and convenient approach for the synthesis of biologically important organophosphorus compounds known as N-(α-phosphoryl)amidophosphates in good to excellent yields. Nitriles with a broad range of additional functionality were tolerated, including those with halides, ethers, amines, and pyridyl groups.