Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-<i>a</i>]pyridines from Diazo Compounds
Peng Zhao, Yanbo Liu, Yuting Zhang, Lei Wang, Yongmin Ma
Abstract
This work demonstrates the synthesis of a variety of perfluoroalkyl heterocycles via a visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/S N V-type/cyclization sequences follow the radical addition reaction of a diazoester, which differs from the current role of diazoesters as radical precursors/acceptors. This transformation demonstrates excellent functional group compatibility and allows for the modification of many bioactive molecules with diazoesters. Such a reaction could represent a novel approach to the photochemical transformation of diazo compounds.
Topics & Concepts
ChemistryDiazoRadical cyclizationCombinatorial chemistryPolarFunctional groupMoleculePhotochemistryStereochemistryOrganic chemistryPhysicsAstronomyPolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry