AI Article Synopsis
- - This study addresses the challenges of using palladium-catalyzed Suzuki-Miyaura couplings with α,β-unsaturated acid derivatives, which are sensitive due to their C=C bonds near carbonyls.
- - A novel selective C-O activation method utilizing superactive triazine esters and organoborons was developed, successfully producing 42 diverse α,β-unsaturated ketones.
- - The research reveals that the dual role of triazine in activating C-O bonds and stabilizing interactions between the catalyst and substrate is crucial for the method's effectiveness and makes it a strong alternative to traditional approaches.
Article Abstract
Palladium-catalysed Suzuki-Miyaura couplings of α,β-unsaturated acid derivatives are challenging due to the susceptibility of their CC 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 α,β-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.
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| http://dx.doi.org/10.1039/d3cc00336a | DOI Listing |
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