A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-02-08 DOI:10.1016/j.tetlet.2025.155504
Lucas Martins Correa Böhs , Calebe Hebrom Livistom Silva , Natália Emanuele Biolosor Kuntz , Benhur Godoi , Andrielli Leitemberger , Marcelo Godoi
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Abstract

Herein we report an efficient and eco-friendly methodology for the selective synthesis of 1,2-bis-organylselanyl alkenes from diorganyl diselenides and terminal alkynes. In this regard, the use of the water extract of rice straw ash (WERSA) proved to be an efficient reaction media promoting the synthesis of the desired compounds in up to 97 % yield with reasonable stereoselectivity. Furthermore, the combination of experimental studies and DFT calculations enabled us to propose a plausible reaction pathway.

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炔双硒化的可持续方法:设计、合成和机理研究
在这里,我们报告了一种高效和环保的方法,用于从二有机二硒化物和末端炔选择性合成1,2-二有机基塞拉烷烯烃。在这方面,使用稻秆灰水提取物(WERSA)被证明是一种有效的反应介质,促进了所需化合物的合成,收率高达97%,具有合理的立体选择性。此外,结合实验研究和DFT计算,我们提出了一个合理的反应途径。
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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Contents continued Graphical abstract TOC Graphical abstract TOC Editorial Board Biocatalytic synthesis of fluorine-containing chiral azido compounds in a two-phase system
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