{"title":"TBN-promoted regioselective C−C bond cleavage: a new strategy for the synthesis of unsymmetrically substituted N-aryl oxalamides","authors":"Guiqin Liu, Zheyan Zhang, Wang Huifeng, Ruiling Chen, Haiying Tian, Xiuling Chen","doi":"10.1039/d4qo01984a","DOIUrl":null,"url":null,"abstract":"Great efforts have been directed toward C-C bond activation and transformation. In contrast, regioselective C−C and C-O bond cleavage and amination is much rare. Here, we report a novel strategy via t-butyl nitrite (TBN) mediated regioselective C−C and C-O bond cleavage for the construction of new C-N bonds. The protocol provides an efficient approach for the synthesis unsymmetrically substituted N-aryl oxalamides using green H2O and TBN as the source of oxygen.The reaction features wide amines substrate scope and good functional tolerance for ester compounds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"201 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-11-30","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/d4qo01984a","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
Great efforts have been directed toward C-C bond activation and transformation. In contrast, regioselective C−C and C-O bond cleavage and amination is much rare. Here, we report a novel strategy via t-butyl nitrite (TBN) mediated regioselective C−C and C-O bond cleavage for the construction of new C-N bonds. The protocol provides an efficient approach for the synthesis unsymmetrically substituted N-aryl oxalamides using green H2O and TBN as the source of oxygen.The reaction features wide amines substrate scope and good functional tolerance for ester compounds.
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.