DrivingRecursive Dehydration by PIII/PV Catalysis:Annulation of Amines and Carboxylic Acids by SequentialC–N and C–C Bond Formation

摘要

A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus P^III/P^V redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C–N and C–C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of P^III/P^V redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the P^III/P^V couple.