Nickel-Catalyzed Cross-Electrophile Coupling between C(sp<sup>2</sup>)–F and C(sp<sup>2</sup>)–Cl Bonds by the Reaction of <i>ortho</i>-Fluoro-Aromatic Amides with Aryl Chlorides
Itsuki Nohira, Naoto Chatani
Abstract
Ni-catalyzed cross-electrophile coupling between C(sp2)–F bonds in ortho-fluoro-substituted aromatic amides and C(sp2)–Cl bonds in aryl chlorides in the presence of Zn as a reductant and LiOtBu as a base, and LiCl and ZnCl2 as additives is reported. The reaction displayed excellent functional group tolerance and a broad substrate scope. The reaction was also applicable to cross-electrophile coupling between C(sp2)–F and C(sp2)–O bonds in an aryl tosylate and a triflate derivative.
Topics & Concepts
ArylElectrophileChemistryTrifluoromethanesulfonateMedicinal chemistryCatalysisCoupling reactionSubstrate (aquarium)StereochemistryOrganic chemistryAlkylOceanographyGeologyCatalytic Cross-Coupling ReactionsFluorine in Organic ChemistryCatalytic C–H Functionalization Methods