{"title":"未活化烯烃与氯仿的光催化氢三氯甲基化反应","authors":"dawei gong, Caiyu Gao, Qixuan Li, Yufei Li, lina zhao, Degong Kong","doi":"10.1039/d4qo01496k","DOIUrl":null,"url":null,"abstract":"Trichloromethyl compounds are essential constituents in synthetic and medicinal chemistry. Hydrotrichloromethylation of alkenes represents the most straightforward approach for synthesizing trichloromethyl compounds. Nonetheless, the applicability of prior synthesis methodologies in this regard was notably constrained by the superstoichiometric use of excessive radical initiators and the formation of alkene polymers or dichloromethylation by-products. Herein, innovative and facile photocatalytic hydrotrichloromethylation of unactivated alkenes using chloroform via base-enabled photoinduced single-electron transfer is demonstrated. This strategy offers an expedited way of synthesizing trichloromethyl compounds with broad applicability and mild conditions while addressing the limitations of previous synthesis methods. Meanwhile, mechanistic studies support the process of chloroform deprotonation followed by oxidation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photocatalytic hydrotrichloromethylation of unactivated alkenes with chloroform\",\"authors\":\"dawei gong, Caiyu Gao, Qixuan Li, Yufei Li, lina zhao, Degong Kong\",\"doi\":\"10.1039/d4qo01496k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Trichloromethyl compounds are essential constituents in synthetic and medicinal chemistry. Hydrotrichloromethylation of alkenes represents the most straightforward approach for synthesizing trichloromethyl compounds. Nonetheless, the applicability of prior synthesis methodologies in this regard was notably constrained by the superstoichiometric use of excessive radical initiators and the formation of alkene polymers or dichloromethylation by-products. Herein, innovative and facile photocatalytic hydrotrichloromethylation of unactivated alkenes using chloroform via base-enabled photoinduced single-electron transfer is demonstrated. This strategy offers an expedited way of synthesizing trichloromethyl compounds with broad applicability and mild conditions while addressing the limitations of previous synthesis methods. Meanwhile, mechanistic studies support the process of chloroform deprotonation followed by oxidation.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-10-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo01496k\",\"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 Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01496k","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Photocatalytic hydrotrichloromethylation of unactivated alkenes with chloroform
Trichloromethyl compounds are essential constituents in synthetic and medicinal chemistry. Hydrotrichloromethylation of alkenes represents the most straightforward approach for synthesizing trichloromethyl compounds. Nonetheless, the applicability of prior synthesis methodologies in this regard was notably constrained by the superstoichiometric use of excessive radical initiators and the formation of alkene polymers or dichloromethylation by-products. Herein, innovative and facile photocatalytic hydrotrichloromethylation of unactivated alkenes using chloroform via base-enabled photoinduced single-electron transfer is demonstrated. This strategy offers an expedited way of synthesizing trichloromethyl compounds with broad applicability and mild conditions while addressing the limitations of previous synthesis methods. Meanwhile, mechanistic studies support the process of chloroform deprotonation followed by oxidation.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.