Zhangqiang Yan , Zhen Zhang , Tao Wen , Lihua Ye , Bo Jin , Chihong Zhang , Wenkun Wang , Zhong-Ning Chen , Hu Cai
{"title":"tBuOK/DMSO/O2催化与苯乙烯的直接α-C（sp3）–H烷基化：氢氨基烷基化的生产性α-氨基†","authors":"Zhangqiang Yan , Zhen Zhang , Tao Wen , Lihua Ye , Bo Jin , Chihong Zhang , Wenkun Wang , Zhong-Ning Chen , Hu Cai","doi":"10.1039/d2qo01911f","DOIUrl":null,"url":null,"abstract":"<div><p>Direct α-C(sp<sup>3</sup>)–H alkylation of hydroaminoalkylation (HAA) catalyzed by <sup><em>t</em></sup>BuOK/DMSO/O<sub>2</sub> from α-aryl benzylamines with styrenes is reported. The reaction has delivered diverse selectively substituted amines and N-heterocycles under mild conditions. Mechanism studies have shown that α-aminoalkyl radicals act as intermediates and hydrogen atom transfer (HAT) plays a crucial role in the <sup><em>t</em></sup>BuOK/DMSO/O<sub>2</sub> system.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2714-2720"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"tBuOK/DMSO/O2 catalyzed direct α-C(sp3)–H alkylation with styrenes: productive α-amino radicals for hydroaminoalkylation†\",\"authors\":\"Zhangqiang Yan , Zhen Zhang , Tao Wen , Lihua Ye , Bo Jin , Chihong Zhang , Wenkun Wang , Zhong-Ning Chen , Hu Cai\",\"doi\":\"10.1039/d2qo01911f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Direct α-C(sp<sup>3</sup>)–H alkylation of hydroaminoalkylation (HAA) catalyzed by <sup><em>t</em></sup>BuOK/DMSO/O<sub>2</sub> from α-aryl benzylamines with styrenes is reported. The reaction has delivered diverse selectively substituted amines and N-heterocycles under mild conditions. Mechanism studies have shown that α-aminoalkyl radicals act as intermediates and hydrogen atom transfer (HAT) plays a crucial role in the <sup><em>t</em></sup>BuOK/DMSO/O<sub>2</sub> system.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 11\",\"pages\":\"Pages 2714-2720\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"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/S2052411023007897\",\"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/S2052411023007897","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
tBuOK/DMSO/O2 catalyzed direct α-C(sp3)–H alkylation with styrenes: productive α-amino radicals for hydroaminoalkylation†
Direct α-C(sp3)–H alkylation of hydroaminoalkylation (HAA) catalyzed by tBuOK/DMSO/O2 from α-aryl benzylamines with styrenes is reported. The reaction has delivered diverse selectively substituted amines and N-heterocycles under mild conditions. Mechanism studies have shown that α-aminoalkyl radicals act as intermediates and hydrogen atom transfer (HAT) plays a crucial role in the tBuOK/DMSO/O2 system.
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