Mingjie Liao , Ziqi Yi , Qingqing You , Chuang Liu , Huangdi Feng , Junhai Huang
{"title":"Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes†","authors":"Mingjie Liao , Ziqi Yi , Qingqing You , Chuang Liu , Huangdi Feng , Junhai Huang","doi":"10.1039/d4qo01780c","DOIUrl":null,"url":null,"abstract":"<div><div>A novel and efficient method for the palladium-catalysed and highly regioselective synthesis of trisubstituted allenes <em>via</em> deaminative coupling of tertiary propargylamines with arylsiloxanes is reported. Both unactivated propargylamines and arylsiloxanes were activated <em>in situ</em> using Et<sub>3</sub>N·3HF, followed by cross-coupling to facilitate C–C bond formation through C–N bond cleavage. The method demonstrates exceptional functional group compatibility, high yields, and readily accessible coupling partners.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 2","pages":"Pages 623-628"},"PeriodicalIF":0.0000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924007824","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/22 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A novel and efficient method for the palladium-catalysed and highly regioselective synthesis of trisubstituted allenes via deaminative coupling of tertiary propargylamines with arylsiloxanes is reported. Both unactivated propargylamines and arylsiloxanes were activated in situ using Et3N·3HF, followed by cross-coupling to facilitate C–C bond formation through C–N bond cleavage. The method demonstrates exceptional functional group compatibility, high yields, and readily accessible coupling partners.