Palladium-Catalyzed C–C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides

• DOI: 10.1021/acs.joc.0c02700
• Publication Date: 2021-01-14T02:05:30Z
• Authors: Tanmayee Nanda; Pragati Biswal; Bedadyuti Vedvyas...; Shyam Kumar Banjare; Ponneri Chandraba...
• Keywords: 01 natural sciences; 0104 chemical sciences

Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.