Luoqiang Zhang , Dao-Yong Zhu , Jingyao Hu , Minjun Feng , Tze Chien Sum , Haoran Sun , Hajime Hirao , Yonggui Robin Chi , Jianrong Steve Zhou
{"title":"追求杂芳烃和脂肪族C–H键的光催化氧化偶联的高效率†","authors":"Luoqiang Zhang , Dao-Yong Zhu , Jingyao Hu , Minjun Feng , Tze Chien Sum , Haoran Sun , Hajime Hirao , Yonggui Robin Chi , Jianrong Steve Zhou","doi":"10.1039/d2qo01558g","DOIUrl":null,"url":null,"abstract":"<div><p>5- and 6-membered heteroarenes, both azoles and azines, were directly alkylated by alkanes, ethers and carbamates using <em>t</em>-butyl peroxybenzoate under LED irradiation. As a serendipitous finding, an organic photosensitizer, 9,10-dichloroanthracene, significantly increased overall efficiency of radical couplings <em>via</em> energy transfer of exciplexes and allowed many examples of oxidative couplings to proceed in good yields, even when 1.5 equivalents of alkanes were used.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1651-1659"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C–H bonds†\",\"authors\":\"Luoqiang Zhang , Dao-Yong Zhu , Jingyao Hu , Minjun Feng , Tze Chien Sum , Haoran Sun , Hajime Hirao , Yonggui Robin Chi , Jianrong Steve Zhou\",\"doi\":\"10.1039/d2qo01558g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>5- and 6-membered heteroarenes, both azoles and azines, were directly alkylated by alkanes, ethers and carbamates using <em>t</em>-butyl peroxybenzoate under LED irradiation. As a serendipitous finding, an organic photosensitizer, 9,10-dichloroanthracene, significantly increased overall efficiency of radical couplings <em>via</em> energy transfer of exciplexes and allowed many examples of oxidative couplings to proceed in good yields, even when 1.5 equivalents of alkanes were used.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 7\",\"pages\":\"Pages 1651-1659\"},\"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/S2052411023005710\",\"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/S2052411023005710","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C–H bonds†
5- and 6-membered heteroarenes, both azoles and azines, were directly alkylated by alkanes, ethers and carbamates using t-butyl peroxybenzoate under LED irradiation. As a serendipitous finding, an organic photosensitizer, 9,10-dichloroanthracene, significantly increased overall efficiency of radical couplings via energy transfer of exciplexes and allowed many examples of oxidative couplings to proceed in good yields, even when 1.5 equivalents of alkanes were used.