1279110-72-3Relevant academic research and scientific papers
Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides
Nanda, Tanmayee,Biswal, Pragati,Pati, Bedadyuti Vedvyas,Banjare, Shyam Kumar,Ravikumar, Ponneri Chandrababu
, p. 2682 - 2695 (2021/02/01)
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.
Palladium-catalyzed hydroesterification of alkynes employing aryl formates without the use of external carbon monoxide
Katafuchi, Yuko,Fujihara, Tetsuaki,Iwai, Tomohiro,Terao, Jun,Tsuji, Yasushi
, p. 475 - 482 (2011/04/22)
A highly efficient hydroesterification of alkynes employing aryl formates has been developed without the use of external carbon monoxide and at ambient pressure. The reaction in the presence of a palladium-xantphos catalyst system selectively affords α,β-unsaturated esters in good to high yields. Use of an aryl formate is crucial and alkyl formates did not react at all. The hydroesterification of norbornene and terminal alkenes also readily proceeded under similar reaction conditions. A mechanistic study showed that conversion of aryl formates to carbon monoxide and phenol derivatives occurred in the hydroesterification. Xantphos is highly effective as a ligand both in the conversion of aryl formates and the hydroesterification reactions.
