Photochemical Decarboxylative C(sp<sup>3</sup>)–X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
Kun‐Quan Chen, Zhixiang Wang, Xiang‐Yu Chen
Abstract
While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C–C bond formations, the corresponding C(sp3)–N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)–X bond formation enabled by the photochemical activity of the NHPI ester–NaI–NHC complex, giving primary C(sp3)–(N)phth, secondary C(sp3)–I, or tertiary C(sp3)–(meta C)phth coupling products. The primary C(sp3)–(N)phth coupling offers convenient access to primary amines.
Topics & Concepts
ChemistryCarbeneReagentPrimary (astronomy)Coupling (piping)AlkylMedicinal chemistryPhotochemistryStereochemistryOrganic chemistryCatalysisPhysicsEngineeringMechanical engineeringAstronomyN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods