{"title":"Facile synthesis of diphosphoryl acetylenes through copper-catalyzed cross coupling","authors":"","doi":"10.1016/j.tetlet.2024.155240","DOIUrl":null,"url":null,"abstract":"<div><p>Organic molecules containing 1,2-diphosphonate moiety are of great value in organic synthesis. Diphosphoryl acetylenes (or named as ethyne-1,2-diyldiphosphonates) are a class of molecules utilized for synthesis of diverse phosphorus compounds applicable in multiple fields. However, present stoichiometric methods for the preparation of diphosphoryl acetylenes generally requires multiple steps or harsh conditions. Herein, we report a facile synthesis of diphosphoryl acetylenes, in which the readily available ethynyl phosphonates couple with dialkyl phosphonates through cheap copper catalysis. A series of diphosphoryl acetylenes in symmetric or unsymmetric fashions are facilely prepared. This protocol demonstrates advantages of mild reaction conditions, inert atmosphere-free, cheap catalyst, base-free, and high efficiency to serve as a practical method for synthesis of diphosphoryl acetylenes.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-08-06","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/S0040403924003356","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
Organic molecules containing 1,2-diphosphonate moiety are of great value in organic synthesis. Diphosphoryl acetylenes (or named as ethyne-1,2-diyldiphosphonates) are a class of molecules utilized for synthesis of diverse phosphorus compounds applicable in multiple fields. However, present stoichiometric methods for the preparation of diphosphoryl acetylenes generally requires multiple steps or harsh conditions. Herein, we report a facile synthesis of diphosphoryl acetylenes, in which the readily available ethynyl phosphonates couple with dialkyl phosphonates through cheap copper catalysis. A series of diphosphoryl acetylenes in symmetric or unsymmetric fashions are facilely prepared. This protocol demonstrates advantages of mild reaction conditions, inert atmosphere-free, cheap catalyst, base-free, and high efficiency to serve as a practical method for synthesis of diphosphoryl acetylenes.
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.