{"title":"可见光诱导C(sp3) -H键与三甲基硅酰氯作为双功能试剂的二氟烷基化","authors":"Xiaochen Wang, Senhui Wu, Pengxuan Ding, Yuxiu Liu, Hong-Jian Song, Qing-Min Wang","doi":"10.1002/adsc.202401497","DOIUrl":null,"url":null,"abstract":"Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"14 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible‐light‐induced Difluoroalkylation of C(sp3)–H Bonds with Trimethylsilyl Chloride as a Dual‐function Reagent\",\"authors\":\"Xiaochen Wang, Senhui Wu, Pengxuan Ding, Yuxiu Liu, Hong-Jian Song, Qing-Min Wang\",\"doi\":\"10.1002/adsc.202401497\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2025-01-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202401497\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401497","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Visible‐light‐induced Difluoroalkylation of C(sp3)–H Bonds with Trimethylsilyl Chloride as a Dual‐function Reagent
Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.