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. 2025 Jan 21;5(2):578-585.
doi: 10.1021/jacsau.4c01182. eCollection 2025 Feb 24.

Copper(I)-Catalyzed Asymmetric α-Selenenylation of 2-Acylimidazoles

Hu Tian  1   2 , Xiaoyu Huang  1   2 , Jun-Zhao Xiao  1 , Liang Yin  1   2
Affiliations

Copper(I)-Catalyzed Asymmetric α-Selenenylation of 2-Acylimidazoles

Hu Tian et al. JACS Au. .

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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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Introduction and Our Working Hypothesis
Scheme 2
Scheme 2. Control Experiments
Figure 1
Figure 1
Investigation of some copper complexes.
Scheme 3
Scheme 3. Transformations of Product 3aa
See this image and copyright information in PMC

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