{"title":"Cathodic Deoxygenative Alkylation of Nitro(hetero)arenes with Organic Halides","authors":"Ziliang Wang, Jianfeng Zhou, Zhouhang Wang, Xueting Zhang, Yikun Ji, Yubing Huang","doi":"10.1021/acs.orglett.4c04792","DOIUrl":null,"url":null,"abstract":"We have realized a cathodic deoxygenative alkylation between nitro(hetero)arenes and organic halides, employing bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) and LiCl as additives to trap and stabilize the generated alkyl radicals and carbanions, thereby facilitating efficient N–O cleavage and selective C–N bond formation. The protocol offers an economical method for the efficient synthesis of multiple aromatic(hetero) amines, without the need for reactive reductants and the exclusion of air and moisture. Notably, the protocol is distinguished by scalability, broad functional group compatibility, and safe and mild conditions, demonstrating practicality in the synthesis and late-stage modification of various bioactive compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04792","RegionNum":1,"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
We have realized a cathodic deoxygenative alkylation between nitro(hetero)arenes and organic halides, employing bis(pinacolato)diboron (B2pin2) and LiCl as additives to trap and stabilize the generated alkyl radicals and carbanions, thereby facilitating efficient N–O cleavage and selective C–N bond formation. The protocol offers an economical method for the efficient synthesis of multiple aromatic(hetero) amines, without the need for reactive reductants and the exclusion of air and moisture. Notably, the protocol is distinguished by scalability, broad functional group compatibility, and safe and mild conditions, demonstrating practicality in the synthesis and late-stage modification of various bioactive compounds.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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