Zhengrui Zhou , Xuliang Tan , Shuyun Peng , Yun Liang , Yuan Yang
{"title":"二甲氧基四甲基二硅烷:克服钯催化的2-碘联苯C-H硅环化的局限性","authors":"Zhengrui Zhou , Xuliang Tan , Shuyun Peng , Yun Liang , Yuan Yang","doi":"10.1039/d5qo00249d","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, a readily accessible silicon reagent (dimethoxytetramethyldisilane) has been developed for time-controlled palladium-catalyzed C–H silacyclization of 2-iodobiphenyls. This protocol enables divergent synthesis of dibenzooxadisilepines and dibenzosiloles in moderate to excellent yields by a process involving palladium-catalyzed disilylation, hydrolysis, condensation, and ring contraction. Notably, this reaction is compatible with a variety of substrates with electron-withdrawing groups, which overcomes the limitations of previous reports.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4031-4036"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Dimethoxytetramethyldisilane: overcoming the limitations of palladium-catalyzed C–H silacyclization of 2-iodobiphenyls†\",\"authors\":\"Zhengrui Zhou , Xuliang Tan , Shuyun Peng , Yun Liang , Yuan Yang\",\"doi\":\"10.1039/d5qo00249d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, a readily accessible silicon reagent (dimethoxytetramethyldisilane) has been developed for time-controlled palladium-catalyzed C–H silacyclization of 2-iodobiphenyls. This protocol enables divergent synthesis of dibenzooxadisilepines and dibenzosiloles in moderate to excellent yields by a process involving palladium-catalyzed disilylation, hydrolysis, condensation, and ring contraction. Notably, this reaction is compatible with a variety of substrates with electron-withdrawing groups, which overcomes the limitations of previous reports.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 14\",\"pages\":\"Pages 4031-4036\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-03-22\",\"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/S2052412925002451\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"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/S2052412925002451","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Dimethoxytetramethyldisilane: overcoming the limitations of palladium-catalyzed C–H silacyclization of 2-iodobiphenyls†
Herein, a readily accessible silicon reagent (dimethoxytetramethyldisilane) has been developed for time-controlled palladium-catalyzed C–H silacyclization of 2-iodobiphenyls. This protocol enables divergent synthesis of dibenzooxadisilepines and dibenzosiloles in moderate to excellent yields by a process involving palladium-catalyzed disilylation, hydrolysis, condensation, and ring contraction. Notably, this reaction is compatible with a variety of substrates with electron-withdrawing groups, which overcomes the limitations of previous reports.