Copper catalyzed tandem Chan–Lam type C—N and Staudinger-phosphite N—P coupling for the synthesis of N-arylphosphoramidates

Abstract

A copper(II)-catalyzed one-pot conversion of aryl/heteroaryl boronic acids to N-aryl phosphoramidates via a tandem Chan–Lam and Staudinger-phosphite coupling has been reported. The method is highly efficient, economical and safe involving in-situ generation of organic azides. The method was successfully extended to boronic esters and potassium organotrifluoroborate salts, however, the organoboranes with B–C(sp3) were found to be unreactive under the reaction conditions. The current method has a wide substrates scope and offers the possibility of synthesizing phosphoramidates in good yield, and notably, the mild reaction conditions used allow for potentially sensitive functionalities to be used in the developed protocol are of great importance in drug discovery.