Kai Jia , Yuan Xue , Daoquan Tu , Jun Luo , Chao Jiang
{"title":"钯催化的分子内C–H胺化，使用硝酸铝作为氧化剂†","authors":"Kai Jia , Yuan Xue , Daoquan Tu , Jun Luo , Chao Jiang","doi":"10.1039/d2qo01562e","DOIUrl":null,"url":null,"abstract":"<div><p>A palladium catalyzed intramolecular C(sp<sup>2</sup>)–H amination using a readily available aluminum nitrate (Al(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O) as the oxidant is reported. The C–H amination is promoted by <em>in situ</em> nitration of the quinoline directing group (DG). The oxindole products can be efficiently converted into novel polycyclic compounds (up to 7 fused rings) <em>via</em> a sequential reduction/cyclization involving the DG. Mechanistic studies indicate that nitration of the quinoline DG favors the following activation of γ-aryl C(sp<sup>2</sup>)–H bonds over β-methyl C(sp<sup>3</sup>)–H bonds.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 109-114"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-catalyzed intramolecular C–H amination using aluminum nitrate as the oxidant†\",\"authors\":\"Kai Jia , Yuan Xue , Daoquan Tu , Jun Luo , Chao Jiang\",\"doi\":\"10.1039/d2qo01562e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A palladium catalyzed intramolecular C(sp<sup>2</sup>)–H amination using a readily available aluminum nitrate (Al(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O) as the oxidant is reported. The C–H amination is promoted by <em>in situ</em> nitration of the quinoline directing group (DG). The oxindole products can be efficiently converted into novel polycyclic compounds (up to 7 fused rings) <em>via</em> a sequential reduction/cyclization involving the DG. Mechanistic studies indicate that nitration of the quinoline DG favors the following activation of γ-aryl C(sp<sup>2</sup>)–H bonds over β-methyl C(sp<sup>3</sup>)–H bonds.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 1\",\"pages\":\"Pages 109-114\"},\"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/S205241102300336X\",\"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/S205241102300336X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Palladium-catalyzed intramolecular C–H amination using aluminum nitrate as the oxidant†
A palladium catalyzed intramolecular C(sp2)–H amination using a readily available aluminum nitrate (Al(NO3)3·9H2O) as the oxidant is reported. The C–H amination is promoted by in situ nitration of the quinoline directing group (DG). The oxindole products can be efficiently converted into novel polycyclic compounds (up to 7 fused rings) via a sequential reduction/cyclization involving the DG. Mechanistic studies indicate that nitration of the quinoline DG favors the following activation of γ-aryl C(sp2)–H bonds over β-methyl C(sp3)–H bonds.
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