Photocatalytic cross-dehydrogenative coupling reaction toward the synthesis of N,N-disubstituted hydrazides and their bromides

Abstract

N,N-Disubstituted hydrazides are useful synthetic building blocks and important pharmaceutical scaffolds in the fields of organo-pharmaceutical chemistry. Direct C(O)–N–N bond formation represents one of the most effective strategies through a cross-dehydrogenative coupling (CDC) process. Here we report an efficient method for the divergent synthesis of N,N-disubstituted hydrazides and their bromides from N,N-disubstituted hydrazines and aldehydes by photoredox-catalytic CDC reactions. This versatile protocol enables the direct construction of C(O)–N–N and C(sp²)–Br bonds simultaneously from available starting materials without prefunctionalization. This one-pot strategy shows the advantages of mild reaction conditions, high atom and step economy, high regioselectivity, as well as good functional group tolerance. In addition, the selected compounds exhibit potential antitumor activities as new chemical entities, thus showing potential applications in the field of new anticancer drug research.