Visible Light Driven and Copper-Catalyzed C(sp<sup>3</sup>)–H Functionalization of <i>O</i>-Pentafluorobenzoyl Ketone Oximes
Danhua Wu, Shuang-Shuang Cui, Fengling Bian, Wei Yu
Abstract
The C(sp3)–H functionalization of O-pentafluorobenzoyl ketone oximes was implemented under visible light irradiation with copper complexes as catalysts. The reactions involve iminyl-radical-mediated intramolecular hydrogen atom transfer as the key step, with the iminyl radicals being generated via copper-effected N–O cleavage. The reaction afforded 3,4-dihydro-2H-pyrroles under the conditions of [Cu(DPEphos)(bcp)]PF6 and DABCO, while γ-pentafluorobenzoyloxy ketones were produced predominantly when [Cu(dpp)2]PF6 and InCl3·4H2O were used as catalysts.
Topics & Concepts
ChemistryKetoneCopperCatalysisSurface modificationDABCOIntramolecular forceRadicalPhotochemistryMedicinal chemistryPolymer chemistryOrganic chemistryPhysical chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions