Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization

Chen-Fan Zhou; Yun-Qian Zhang; Yong Ling; Liang Ming; Xia Xi; Gong-Qing Liu; Yanan Zhang

doi:10.1039/D1OB02196F

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Time-economical synthesis of selenofunctionalized heterocycles via I₂O₅-mediated selenylative heterocyclization†

Chen-Fan Zhou,^a Yun-Qian Zhang,^a Yong Ling,^a Liang Ming,^a Xia Xi,^a Gong-Qing Liu

*^a and Yanan Zhang*^a

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* Corresponding authors

^a School of Pharmacy, Nantong University, 19 Qixiu Road, Nantong 226001, People's Republic of China
E-mail: gqliu@ntu.edu.cn, zhangyanan@gmail.com

Abstract

A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I₂O₅-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were synthesized with up to 97% isolated yield in minutes. Additional features of this new protocol include the use of an inorganic oxidant, mild conditions, and easy operation. Preliminary investigations suggest that the transformation operates through selenenyl iodide-induced electrophilic cyclization.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB02196F
Article type: Paper
Submitted: 10 Nov 2021
Accepted: 03 Dec 2021
First published: 03 Dec 2021

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Org. Biomol. Chem., 2022,20, 420-426

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Time-economical synthesis of selenofunctionalized heterocycles via I₂O₅-mediated selenylative heterocyclization

C. Zhou, Y. Zhang, Y. Ling, L. Ming, X. Xi, G. Liu and Y. Zhang, Org. Biomol. Chem., 2022, 20, 420 DOI: 10.1039/D1OB02196F

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Organic & Biomolecular Chemistry