Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

• Acylative Suzuki coupling of active amides with high-order arylborons has been achieved.
• All of aryl groups of diarylborinic acids or sodium tetraarylborates could be efficiently used as the aryl sources.
• A variety of aryl ketones including sterically hindered ones could be synthesized.

A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)2Cl2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides.

Figure optionsDownload as PowerPoint slide