{"title":"可见光驱动的光催化级联多氧化：α-亚砜基酞的一条途径。","authors":"Dabao Tan, Lele Zhang, Qihu Yang, Xiang Li, Hongjin Lian, Feiming Li, Zhixiong Cai, Lina Cai* and Shunyou Cai*, ","doi":"10.1021/acs.orglett.5c02462","DOIUrl":null,"url":null,"abstract":"<p >The integration of direct C(sp<sup>3</sup>)–H functionalization with tandem reactions offers a strategy for the synthesis of complex, high-value fine chemicals from basic chemical feedstocks. This paper presents an efficient synthetic pathway for the olefinic difunctionalization of <i>o</i>-methylstyrenes using thiophenols, followed by oxidative dehydrogenative lactonization catalyzed by LaBr<sub>3</sub> under visible light irradiation. This approach enables the facile synthesis of a wide range of α-sulfinylphthalides with moderate diastereoselectivity. Notably, the reaction does not require additional photosensitizers or strong oxidants; mild conditions suffice under an oxygen atmosphere. Mechanistic studies and control experiments have confirmed the essential role of LaBr<sub>3</sub> in this process.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 33","pages":"9141–9147"},"PeriodicalIF":5.0000,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-Light-Driven Photocatalytic Cascade Multioxidation: A Route to α-Sulfinylphthalides\",\"authors\":\"Dabao Tan, Lele Zhang, Qihu Yang, Xiang Li, Hongjin Lian, Feiming Li, Zhixiong Cai, Lina Cai* and Shunyou Cai*, \",\"doi\":\"10.1021/acs.orglett.5c02462\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The integration of direct C(sp<sup>3</sup>)–H functionalization with tandem reactions offers a strategy for the synthesis of complex, high-value fine chemicals from basic chemical feedstocks. This paper presents an efficient synthetic pathway for the olefinic difunctionalization of <i>o</i>-methylstyrenes using thiophenols, followed by oxidative dehydrogenative lactonization catalyzed by LaBr<sub>3</sub> under visible light irradiation. This approach enables the facile synthesis of a wide range of α-sulfinylphthalides with moderate diastereoselectivity. Notably, the reaction does not require additional photosensitizers or strong oxidants; mild conditions suffice under an oxygen atmosphere. Mechanistic studies and control experiments have confirmed the essential role of LaBr<sub>3</sub> in this process.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 33\",\"pages\":\"9141–9147\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-08-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c02462\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c02462","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Visible-Light-Driven Photocatalytic Cascade Multioxidation: A Route to α-Sulfinylphthalides
The integration of direct C(sp3)–H functionalization with tandem reactions offers a strategy for the synthesis of complex, high-value fine chemicals from basic chemical feedstocks. This paper presents an efficient synthetic pathway for the olefinic difunctionalization of o-methylstyrenes using thiophenols, followed by oxidative dehydrogenative lactonization catalyzed by LaBr3 under visible light irradiation. This approach enables the facile synthesis of a wide range of α-sulfinylphthalides with moderate diastereoselectivity. Notably, the reaction does not require additional photosensitizers or strong oxidants; mild conditions suffice under an oxygen atmosphere. Mechanistic studies and control experiments have confirmed the essential role of LaBr3 in this process.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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