NHC-Catalyzed Radical Cross-Claisen Condensation for Diverse β-Keto Ester Synthesis
Xiangyu Zhuang , Hao Li , Hongyu Wang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (22) : 2997 -3002.
NHC-Catalyzed Radical Cross-Claisen Condensation for Diverse β-Keto Ester Synthesis
The cross-Claisen condensation is a valuable method for synthesizing β-keto esters but is traditionally limited by the need for strong bases or preformed silyl ketene acetals (SKAs) or a narrow substrate scope. To address these challenges, we developed a mild, N-heterocyclic carbene (NHC)-catalyzed radical cross-Claisen condensation between acyl imidazoles and α-bromo esters. This protocol employs Mn-mediated single-electron reduction to generate persistent ketyl and α-carbonyl radicals, enabling efficient cross-coupling of two electrophiles under redox-neutral conditions. The reaction proceeds with broad functional-group tolerance and can be conducted in a one-pot manner directly from carboxylic acids, offering a practical platform for β-keto ester synthesis.
Cross-Claisen condensation / Radical / NHC catalysis / β-keto ester / Cross-electrophile coupling
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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