Souvik Chatterjee, Sabnam Azmi, Nilaj Bandopadhyay, Krishnendu Paramanik, Gayetri Sarkar, Bhaskar Biswas, Hari Sankar Das
{"title":"Benzylamine promoted direct C-H arylation of arenes and heteroarenes <i>via</i> excitation with heat or light.","authors":"Souvik Chatterjee, Sabnam Azmi, Nilaj Bandopadhyay, Krishnendu Paramanik, Gayetri Sarkar, Bhaskar Biswas, Hari Sankar Das","doi":"10.1039/d4ob01377h","DOIUrl":null,"url":null,"abstract":"<p><p>Carbon-halogen bond cleavage in aryl halides through single electron transfer (SET) is a crucial step in radical-based cross-coupling reactions. Accomplishing such cleavage using an organic system without the assistance of any transition metal-based catalyst is highly challenging. In recent years, combining organic molecules and a base has served as a unique system for SET-mediated carbon-halogen bond cleavage. Herein, we report the combination of simple benzylamine and potassium <i>tert</i>-butoxide as a super-electron-donor system for SET-mediated cleavage of aryl halides generating reactive aryl radicals, which subsequently react with arenes or heteroarenes and produce biaryl skeletons. The new methodology enables the arylation of arenes and heteroarenes with aryl iodides, or aryl bromides, upon excitation with heat or light. The broad substrate scope, mild reaction conditions and tolerance of common organic functional groups offer an efficient alternative route for direct C-H arylation reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-10-21","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/d4ob01377h","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
Carbon-halogen bond cleavage in aryl halides through single electron transfer (SET) is a crucial step in radical-based cross-coupling reactions. Accomplishing such cleavage using an organic system without the assistance of any transition metal-based catalyst is highly challenging. In recent years, combining organic molecules and a base has served as a unique system for SET-mediated carbon-halogen bond cleavage. Herein, we report the combination of simple benzylamine and potassium tert-butoxide as a super-electron-donor system for SET-mediated cleavage of aryl halides generating reactive aryl radicals, which subsequently react with arenes or heteroarenes and produce biaryl skeletons. The new methodology enables the arylation of arenes and heteroarenes with aryl iodides, or aryl bromides, upon excitation with heat or light. The broad substrate scope, mild reaction conditions and tolerance of common organic functional groups offer an efficient alternative route for direct C-H arylation reactions.