Adrian Tlahuext-Aca, Quyen D Nguyen, Yang Gao, Girish C Sati, Jinpeng Zhao, Daniel Valco
{"title":"Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions.","authors":"Adrian Tlahuext-Aca, Quyen D Nguyen, Yang Gao, Girish C Sati, Jinpeng Zhao, Daniel Valco","doi":"10.1021/acs.joc.4c01499","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we disclose a palladium-catalyzed cross-coupling of aryl bromides and chlorides with trimethylsilylalkynes under mild reaction conditions. This method utilizes commercially available and air stable palladium precatalysts and avoids the use of copper cocatalysts. Moreover, it allows for the synthesis of a wide range of disubstituted alkynes in high yields with excellent functional group tolerance. The utility of the developed method was further demonstrated via the late-stage alkynylation of pharmaceuticals and natural bioactive compounds.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01499","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/2 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we disclose a palladium-catalyzed cross-coupling of aryl bromides and chlorides with trimethylsilylalkynes under mild reaction conditions. This method utilizes commercially available and air stable palladium precatalysts and avoids the use of copper cocatalysts. Moreover, it allows for the synthesis of a wide range of disubstituted alkynes in high yields with excellent functional group tolerance. The utility of the developed method was further demonstrated via the late-stage alkynylation of pharmaceuticals and natural bioactive compounds.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.