{"title":"A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies","authors":"Lucas Martins Correa Böhs , Calebe Hebrom Livistom Silva , Natália Emanuele Biolosor Kuntz , Benhur Godoi , Andrielli Leitemberger , Marcelo Godoi","doi":"10.1016/j.tetlet.2025.155504","DOIUrl":null,"url":null,"abstract":"<div><div>Herein we report an efficient and eco-friendly methodology for the selective synthesis of 1,2-<em>bis</em>-organylselanyl alkenes from diorganyl diselenides and terminal alkynes. In this regard, the use of the water extract of rice straw ash (<em>WERSA</em>) 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.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155504"},"PeriodicalIF":1.5000,"publicationDate":"2025-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040392500053X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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.
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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