Linfeng Liu , Yujian Pang , Canliang Ma , Daiqing Zhou , Wenjie Zhang , Jin Huang , Jie Sun , Jiangkai Qiu , Yihuan Liu , Lei Shen , Zhenjiang Li , Kai Guo
{"title":"通过光氧化催化实现硫代磺酸盐与 C(sp3)-H 的直接官能化","authors":"Linfeng Liu , Yujian Pang , Canliang Ma , Daiqing Zhou , Wenjie Zhang , Jin Huang , Jie Sun , Jiangkai Qiu , Yihuan Liu , Lei Shen , Zhenjiang Li , Kai Guo","doi":"10.1016/j.gresc.2024.05.003","DOIUrl":null,"url":null,"abstract":"<div><div>While C(sp<sup>3</sup>)-S bonds exist in many biologically active compounds, the direct catalytic C(sp<sup>3</sup>)-H thiolation remains elusive. Herein, we report a convenient and green C(sp<sup>3</sup>)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp<sup>3</sup>)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 4","pages":"Pages 453-458"},"PeriodicalIF":0.0000,"publicationDate":"2025-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Direct C(sp3)-H functionalization with thiosulfonates via photoredox catalysis\",\"authors\":\"Linfeng Liu , Yujian Pang , Canliang Ma , Daiqing Zhou , Wenjie Zhang , Jin Huang , Jie Sun , Jiangkai Qiu , Yihuan Liu , Lei Shen , Zhenjiang Li , Kai Guo\",\"doi\":\"10.1016/j.gresc.2024.05.003\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>While C(sp<sup>3</sup>)-S bonds exist in many biologically active compounds, the direct catalytic C(sp<sup>3</sup>)-H thiolation remains elusive. Herein, we report a convenient and green C(sp<sup>3</sup>)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp<sup>3</sup>)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.</div></div>\",\"PeriodicalId\":12794,\"journal\":{\"name\":\"Green Synthesis and Catalysis\",\"volume\":\"6 4\",\"pages\":\"Pages 453-458\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-11-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Synthesis and Catalysis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666554924000565\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/5/20 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666554924000565","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/5/20 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Direct C(sp3)-H functionalization with thiosulfonates via photoredox catalysis
While C(sp3)-S bonds exist in many biologically active compounds, the direct catalytic C(sp3)-H thiolation remains elusive. Herein, we report a convenient and green C(sp3)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp3)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.
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