A Nickel Pre-Catalyst for the O -Arylation of Primary, Secondary, and Tertiary Alcohols with (Hetero)aryl Chlorides

While base metal-catalyzed cross-couplings of alcohols and (hetero)aryl chlorides have emerged over the past decade, the development of a single pre-catalyst capable of promoting such transformations spanning all of primary, secondary, and tertiary (aliphatic) alcohols remains an enduring challenge. Herein we disclose the easily prepared, air-stable 4-cyanophenyl pre-catalyst (L2)Ni(4-CN-Ph)Cl (L2 = CgPhen-DalPhos), which is shown to be capable of promoting, with useful reaction scope, the C–O cross-coupling of all such alcohol classes with (hetero)aryl chlorides.