Palladium-catalysed Suzuki-Miyaura coupling of α,β-unsaturated superactive triazine esters

Palladium-catalysed Suzuki-Miyaura couplings of a,b-unsaturated acid derivatives are challenging due to the susceptibility of their C=C bonds adjacent to carbonyl groups. In this work, we describe a highly selective C-O activation approach to this transformation using superactive triazine esters and organoborons as coupling partners. 42 alpha,beta-unsaturated ketones with diverse functional groups have been prepared with this method. The mechanistic investigation unveiled that the dual function of triazine for activating the C-O bond and stabilizing non-covalent interactions between the catalyst and substrate is critical for the reaction's success. The method's efficiency, functional group compatibility and unique mechanism make it a valuable alternative to classic methods.

Automated summary

In this study, a highly selective C-O activation approach using superactive triazine esters and organoborons as coupling partners was developed for the synthesis of α,β-unsaturated ketones with diverse functional groups. Mechanistic investigation revealed that the dual function of triazine for activating the C-O bond and stabilizing non-covalent interactions between the catalyst and substrate is critical for the reaction's success. The method's efficiency, functional group compatibility, and unique mechanism make it a valuable alternative to classic methods.