Defunctionalization of sp<sup>3</sup> C–Heteroatom and sp<sup>3</sup> C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts
Yiting Gu, Hongfei Yin, Matthew G. Wakeling, Juzeng An, Rubén Martı́n
Abstract
A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.
Topics & Concepts
HeteroatomCatalysisChemistryKetoneKetylPhotochemistryMedicinal chemistryBenzophenoneOrganic chemistryRing (chemistry)Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques