{"title":"钌催化的1,3-吲哚基在α,α-二取代烯丙醇中的迁移","authors":"Xue Zhang , Zhen Luo , Tang-Lin Liu , Qing-Hua Li","doi":"10.1039/d3qo00049d","DOIUrl":null,"url":null,"abstract":"<div><p>The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1705-1709"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols†\",\"authors\":\"Xue Zhang , Zhen Luo , Tang-Lin Liu , Qing-Hua Li\",\"doi\":\"10.1039/d3qo00049d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 7\",\"pages\":\"Pages 1705-1709\"},\"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/S2052411023005862\",\"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/S2052411023005862","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols†
The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp3)–C(sp2) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.