N-fluorobenzenesulfonimide (NFSI)-mediated rapid regioselective oxyselenation of internal alkenes with diselenides

Li-Qiu Liu; Jiu-Ling Li; Ying-Chun Wang; Heng-Shan Wang

Results in Chemistry (Jan 2021)

N-fluorobenzenesulfonimide (NFSI)-mediated rapid regioselective oxyselenation of internal alkenes with diselenides

Li-Qiu Liu,
Jiu-Ling Li,
Ying-Chun Wang,
Heng-Shan Wang

Affiliations

Li-Qiu Liu: College of Chemistry and Chemical Engineering, Hunan Engineering Laboratory forAnalyse and Drugs Development of Ethnomedicine in Wuling Mountains, Jishou University, Jishou 416000, People’s Republic of China
Jiu-Ling Li: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and PharmaceuticalSciences of Guangxi, Normal University, Guilin 541004, People’s Republic of China
Ying-Chun Wang: College of Chemistry and Chemical Engineering, Hunan Engineering Laboratory forAnalyse and Drugs Development of Ethnomedicine in Wuling Mountains, Jishou University, Jishou 416000, People’s Republic of China; Corresponding authors.
Heng-Shan Wang: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and PharmaceuticalSciences of Guangxi, Normal University, Guilin 541004, People’s Republic of China; Corresponding authors.

Journal volume & issue: Vol. 3
p. 100220

Abstract

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A rapid and efficient NFSI-mediated hydroxy or alkoxy-selenation of internal alkenes and chalcones is presented. This reaction proceeds smoothly at room temperature and features broad substrate scope, which employs NFSI as the oxidizing agent, affording β-hydroxy(alkoxy)selenides with excellent yields and high regioselectivity. An electrophilic mechanism is proposed for the transformation.

Published in Results in Chemistry

ISSN: 2211-7156 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: https://www.journals.elsevier.com/results-in-chemistry/

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