Remote Regioselective Radical C–H Functionalization of Unactivated C–H Bonds in Amides: The Synthesis of <i>gem</i>-Difluoroalkenes
Qu-Ping Hu, Jing Cheng, Ying Wang, Jie Shi, Bi‐Qin Wang, Ping Hu, Ke‐Qing Zhao, Fei Pan
Abstract
The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)–H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.
Topics & Concepts
ChemistrySurface modificationRegioselectivitySelectivityAmideRadicalCombinatorial chemistryTrifluoromethylPrimary (astronomy)Hydrogen atomHydrogen bondOrganic chemistryMoleculeCatalysisGroup (periodic table)Physical chemistryAlkylPhysicsAstronomyFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods