Visible-Light-Mediated<i>N</i>-Desulfonylation of<i>N</i>-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst
Cameron J. Hunter, Michael J. Boyd, Gregory D. May, Robert Fimognari
Abstract
A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.
Topics & Concepts
ChemistryBenzimidazolePhotocatalysisPhotoredox catalysisCopperFunctional groupPhotochemistryCombinatorial chemistryVisible spectrumMedicinal chemistryOrganic chemistryCatalysisPolymerPhysicsOptoelectronicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods