Nickel-catalyzed Hydrodefluorination of ortho-Fluoro Aromatic Amides with 2-Propanol

Nickel-Catalyzed Functionalization Reactions Involving C–H Bond Activation via an Amidate-Promoted Strategy and Its Extension to the Activation of C–F, C–O, C–S, and C–CN Bonds

“…Several control experiments and stochiometric studies using the catalytically relevant, isolable azanickelacycle 32 supported a mechanism in which an organozinc nucleophile is generated from Ph–Cl and Zn under the reaction conditions. This strategy was also applicable to Suzuki–Miyaura cross coupling (Scheme B) and hydrodefluorination with inexpensive reagents, such as NaBH 4 and 2-propanol as hydride sources (Scheme C) . When the substrates contain multiple C–F bonds, only the C–F bond at the ortho position reacted, indicating the facile generation of an azanickelacycle intermediate, accompanied by the selective activation of the ortho C–F bond through chelation assistance.…”