Nickel-Catalyzed Cross-Electrophile Coupling between C(sp2)-F and C(sp2)-Cl Bonds by the Reaction of ortho-Fluoro-Aromatic Amides with Aryl Chlorides

Ni-catalyzed cross-electrophile coupling between C(sp(2))-F bonds in ortho-fluoro-substituted aromatic amides and C(sp(2))-Cl bonds in aryl chlorides in the presence of Zn as a reductant and (LiOBu)-Bu-t 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(sp(2))-F and C(sp(2))-O bonds in an aryl tosylate and a triflate derivative.

Automated summary

In this study, a Ni-catalyzed cross-electrophile coupling between C(sp(2))-F bonds in ortho-fluoro-substituted aromatic amides and C(sp(2))-Cl bonds in aryl chlorides was reported. The reaction, using Zn as a reductant and (LiOBu)-Bu-t as a base, with LiCl and ZnCl2 as additives, displayed excellent functional group tolerance and a broad substrate scope. Furthermore, the reaction was also applicable to cross-electrophile coupling between C(sp(2))-F and C(sp(2))-O bonds in an aryl tosylate and a triflate derivative.