Nickel-Catalyzed Ortho-Arylation of Unactivated (Hetero)aryl C-H Bonds with Arylsilanes Using a Removable Auxiliary.

Ni(II)-catalyzed ortho-arylation of aromatic and heteroaromatic carboxamides with triethoxy(aryl)silanes assisted by a removable bidentate auxiliary is reported. This transformation features a broad substrate scope, good functional group tolerance, and compatibility with heterocyclic substrates. Compared to the well-established Ni(II)-catalyzed C-H arylation with ArX or aryliodonium salts via oxidative addition, this reaction proceeded via a fluoride-promoted transmetalation.