Selective N -functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh 3 /DDQ System.

We present a PPh 3 /DDQ-mediated regiospecific selective N -functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis of N 1 -benzyl arylhydrazines and N 2 -acyl arylhydrazines, respectively. This metal- and base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, and mild reaction conditions. Furthermore, N 1 -benzlated products have also been successfully applied to the concise synthesis of N -substituted indoles and anticancer drug MDM2 inhibitor.