Nickel-catalyzed Suzuki-Miyaura cross-coupling of C-F bonds

The efficient Suzuki-Miyaura cross-coupling of ortho-fluoro aromatic secondary amides with aryl boronates is described. The use of (KOBu)-Bu-t is essential for the reaction to proceed. The function of the base is to abstract a proton from an amide nitrogen to generate a weak conjugate base, such as an amidate, which functions as a directing group. The reaction proceeds effectively, even at 60 degrees C. The reaction exhibits a good tolerance for functional groups and a broad scope for aromatic amides.

Automated summary

The efficient Suzuki-Miyaura cross-coupling of ortho-fluoro aromatic secondary amides with aryl boronates is achieved using (KOBu)-Bu-t as an essential reactant. The base serves to extract a proton from the amide nitrogen, generating a weak conjugate base that acts as a directing group. The reaction demonstrates good tolerance for functional groups and a broad scope for aromatic amides, even at 60 degrees C.