Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp<sup>3</sup>)–H/C(sp<sup>3</sup>)–H and C(sp<sup>3</sup>)–H/C(sp<sup>2</sup>)–H via Intermolecular HAT
Xinpeng Xie, Kaikai Qiao, Bing-ru Shao, Wenfeng Jiang, Lei Shi
Abstract
Cross-dehydrogenative coupling has emerged as a robust tool to construct C–C and C–heteroatom bonds. Herein, we reported an interesting visible-light-mediated radical CDC of C(sp 3 )–H/C(sp 3 )–H and C(sp 3 )–H/C(sp 2 )–H, enabled by a phenyl radical guided intermolecular HAT process. This strategy allowed the efficient coupling of a wide range of inert C(sp 3 )–H and C(sp 2 )–H with α-N C(sp 3 )–H of amines in good regioselectivities and yields. Mechanistic studies indicate that the EDA complex triggered an intermolecular HAT process.
Topics & Concepts
ChemistryIntermolecular forceHeteroatomCoupling (piping)StereochemistryCrystallographyMoleculeOrganic chemistryRing (chemistry)Mechanical engineeringEngineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques