Synthesis of α-Aminophosphonates via Phosphonylation of an Aryne-Imine Adduct

J Org Chem. 2020 Oct 16;85(20):13246-13255. doi: 10.1021/acs.joc.0c01410. Epub 2020 Sep 23.

Abstract

Multicomponent phosphonylation is accomplished upon the reaction of an imine with an aryne generated in situ in the presence of a dialkyl phosphite. This transition-metal-free protocol shows a broad substrate scope, providing a variety of α-aminophosphonates in moderate to good yields. A plausible mechanism for the reaction is proposed based on a deuterium exchange experiment.