Ni(ii)/BINOL-catalyzed alkenylation of unactivated C(sp3)–H bonds

Abstract

The first nickel-catalyzed alkenylation of unactivated C(sp³)–H bonds with vinyl iodides is described. The catalytic system comprises an inexpensive and air-stable Ni(acac)₂ as the catalyst and BINOL as the ligand, which is highly efficient for the alkenylation of β-methyl C(sp³)–H bonds of a broad range of aliphatic carboxamides. The resulting olefins can serve as versatile handles for further preparation. Additionally, we also demonstrated the synthesis of functionalized carboxamides bearing α-quaternary carbon centers from simple pivalamide via nickel-catalyzed sequential C(sp³)–H bond functionalization.