Global Research Center(GRC)早稲田大学 研究活動 Research Activities

Selective C–N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis(Published in Journal of the American Chemical Society, October 2024)

Journal Title
/掲載ジャーナル名
Journal of the American Chemical Society
Publication Year and Month
/掲載年月
October, 2024
Paper Title
/論文タイトル
Selective C–N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis
DOI
/論文DOI
10.1021/jacs.4c13210
 Author of Waseda University
/本学の著者
AIDA, Kazuhiro(Student, Faculty of Science and Engineering, Graduate School of Advanced Science and Engineering):Lasr Author
Related Websites
/関連Web
Abstract
/抄録
Cleavage of inert C–N bonds in unstrained azacycles such as pyrrolidine remains a formidable challenge in synthetic chemistry. To address this, we introduce an effective strategy for the reductive cleavage of the C–N bond in N-benzoyl pyrrolidine, leveraging a combination of Lewis acid and photoredox catalysis. This method involves single-electron transfer to the amide, followed by site-selective cleavage at the C2–N bond. Cyclic voltammetry and NMR studies demonstrated that the Lewis acid is crucial for promoting the single-electron transfer from the photoredox catalyst to the amide carbonyl group. This protocol is widely applicable to various pyrrolidine-containing molecules and enables inert C–N bond cleavage including C–C bond formation via intermolecular radical addition. Furthermore, the current protocol successfully converts pyrrolidines to aziridines, γ-lactones, and tetrahydrofurans, showcasing its potential of the inert C–N bond cleavage for expanding synthetic strategies.
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