Mingjie Liao , Ziqi Yi , Qingqing You , Chuang Liu , Huangdi Feng , Junhai Huang
{"title":"通过钯催化三级丙炔胺与芳基硅氧烷的脱氨基偶联高效合成三取代烯烃","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":"{\"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}","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}
Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes†
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.