Visible-Light-Induced Reductive Coupling of Arylacetylenes with Benzothiazole Sulfones.

Autor: Sengoku T; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan., Iwama H; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan., Shimotori T; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan., Fujimoto K; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan., Inuzuka T; Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan., Matsune K; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan., Yoda H; Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Sep 01; Vol. 88 (17), pp. 12776-12782. Date of Electronic Publication: 2023 Aug 23.
DOI: 10.1021/acs.joc.3c01554
Abstrakt: In this study, we propose heavy-metal-free reductive coupling of arylacetylenes with benzothiazole sulfones. The reactions of alkyl or benzylic benzothiazole sulfones with arylacetylenes are successfully performed in the presence of Hantzsch esters and K 2 CO 3 under visible-light irradiation to afford 1,2-disubstituted alkenes in moderate to good yields, with Z -isomer as the major product. The utility of this protocol is expanded to α-deuterative coupling using a deuterated Hantzsch ester, furnishing the corresponding alkenes with high deuterium incorporation.
Databáze: MEDLINE
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