Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene

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(sp(3))-N bond formation is still in its infancy. We demonstrate herein transitionmetal-free decarboxylative C(sp(3))-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp(3))-(N)phth, secondary C(sp(3))-I, or tertiary C(sp(3))(meta C)phth coupling products. The primary C(sp(3))-(N)phth coupling offers convenient access to primary amines.