Base-Promoted Reactions of Organostibines with Alkynes and Organic Halides to Give Chalcogenated (Z)‑Olefins and Ethers

Herein, with air-stable chalcogenated stibines (Sb–ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydro­chalcogenation of alkynes with DMSO/DMSO-d 6 as hydrogen/deuterium sources, giving chalcogenated (Z)-olefins in good yields and with excellent regioselectivity. Thes...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (33), p.6159-6164
Main Authors: Le, Liyuan, Li, Shuangshuang, Zhang, Dejiang, Yin, Shuang-Feng, Kambe, Nobuaki, Qiu, Renhua
Format: Article
Language:English
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Summary:Herein, with air-stable chalcogenated stibines (Sb–ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydro­chalcogenation of alkynes with DMSO/DMSO-d 6 as hydrogen/deuterium sources, giving chalcogenated (Z)-olefins in good yields and with excellent regioselectivity. These reagents, easily synthesized from halostibines with in situ generated [Zn­(ER)2] at room temperature within a few minutes, could be also used in the base-promoted C­(sp 3)–S­(Se) cross-coupling with C­(sp 3)–X and copper-catalyzed C­(sp 2)–S­(Se) cross-coupling with C­(sp 2)–X (X = F, CI, Br, I) under mild conditions. This protocol could also be simply extended to organobismuth complexes (Bi–ER) with good functional tolerance.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02369