{"title":"Dichlorination of olefins with trichloroisocyanuric acid (TCCA) and tetrabutylammonium chloride (TBACl).","authors":"Ramazan Koçak","doi":"10.1039/d4ob01962h","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, <i>α</i>,<i>β</i>-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01962h","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, α,β-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
