Metal- and Base-Free Electrophilic Addition of 3-Diazooxindoles with H-phosphine Oxides for N–P Bond Formation

Abstract

A highly efficient electrophilic addition of 3-diazooxindoles to H-phosphine oxides under metal-free and base-free conditions is established, leading to phosphinic hydrazides. This method has good chemoselectivity and broad substrate diversity, and provides a facile and green approach for N–P bond formation. The stereoselective synthesis represents a unique example of asymmetric electrophilic addition of diazo compounds as N-terminal electrophiles with phosphorus compounds, affording P-stereogenic phosphinic hydrazides with excellent stereoselectivity.