Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)–H Bonds via Hydrogen Atom Transfer

We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C­(sp3)–H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of substituted alkene and alkyne compounds were synthesized in high yields with good regioselectivity and functional-group compatibility. Late-stage functionalization of natural products and drug molecules is also demonstrated.