Boron Chelates Derived from <i>N</i>-Acylhydrazones as Radical Acceptors: Photocatalyzed Coupling of Hydrazones with Carboxylic Acids
Igor A. Dmitriev, Vitalij V. Levin, Alexander D. Dilman
Abstract
Difluoroboryl complexes obtained from N-acyl hydrazones upon brief treatment with boron trifluoride and allylic silane serve as efficient acceptors of alkyl radicals. The reaction of the boryl chelates with carboxylic acids in the presence of an acridine-type photocatalyst leading to N-acyl hydrazides is described. The efficiency of addition at the C═N bond of the chelates is determined by the formation of a nitrogen-centered radical stabilized by the boron-containing heterocyclic ring.
Topics & Concepts
ChemistryBoron trifluorideAllylic rearrangementChelationRadicalBoronSilaneAlkylMedicinal chemistryDouble bondOrganic chemistryPhotochemistryPolymer chemistryCatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques