Electron-Transfer Protocol for the Hydroxyalkenylation of Alkenes Using 1,2-Bis(phenylsulfonyl)ethylene.

Autor: Tsai CY; Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu, 30010, Taiwan., Jhang YJ; Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu, 30010, Taiwan., Wu YK; Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu, 30010, Taiwan., Ryu I; Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu, 30010, Taiwan.; Organization for Research Promotion, Osaka Metropolitan University (OMU), 599-8531, Sakai, Osaka, Japan.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Dec 04; Vol. 62 (49), pp. e202311807. Date of Electronic Publication: 2023 Oct 31.
DOI: 10.1002/anie.202311807
Abstrakt: We report a protocol for alkene hydroxyalkenylation. Using a persulfate anion as a one-electron-oxidation reagent and 1,2-bis(phenylsulfonyl)ethylene as a radical acceptor in the presence of water, alkenes were converted into the corresponding 1-phenylsulfonyl-4-hydroxyalkenes in good to high yields. The hydroxyalkenylation process involves the nucleophilic hydroxylation of alkene radical cations to give β-hydroxyalkyl radicals, which, after a radical addition/β-elimination sequence, provide the products. We also report a photocatalytic protocol for alkoxyalkenylation.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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