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Updated: May 25, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper(I)-Catalyzed Asymmetric α-Selenenylation of 2-Acylimidazoles
Hu Tian1,2, Xiaoyu Huang1,2, Jun-Zhao Xiao1
1School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, Henan China.
Abstract:
A general method for the catalytic asymmetric α-selenenylation of simple carbonyl compounds is lacking. Herein, a copper(I)-catalyzed enantioselective α-selenenylation of 2-acylimidazoles with electrophilic selenosulfonates is uncovered. The reaction enjoys the advantages of mild conditions, easy reaction protocol, and broad substrate scopes on both 2-acylimidazoles and selenosulfonates. Mechanistic studies reveal a pincer Cu(I)-(S,S)-Ph-BOPA complex as the active catalyst. Some traditional electrophilic selenenylation reagents, such as PhSeCl, PhSeSePh, and 2-(phenylselanyl)isoindoline-1,3-dione lead to inferior results in terms of both yield and enantioselectivity, highlighting the superiority of selenosulfonates. Finally, several transformations based on both the 2-acylimidazole group and the selenoether group are successfully carried out, demonstrating the synthetic utilities of the present methodology.
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