{"title":"Synthesis of Secondary Boronates via Deaminative Cross-Coupling of Alkyl Nitroso Carbamates and Boronic Acids","authors":"Shashwati Paul, Prof. M. Kevin Brown","doi":"10.1002/ange.202408432","DOIUrl":null,"url":null,"abstract":"<p>A strategy for transition metal-free cross-coupling of alkyl nitroso-carbamates and boronic acids is reported. The <i>N</i>-nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows for the synthesis of a wide variety of secondary boronates, benzylic boronates and formal Csp<sup>3</sup>−Csp<sup>2</sup> cross-coupling products under operationally simple conditions. Functional group tolerance is also demonstrated and applied in the modification of lysine to make non-canonical amino acids.</p>","PeriodicalId":7803,"journal":{"name":"Angewandte Chemie","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ange.202408432","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ange.202408432","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A strategy for transition metal-free cross-coupling of alkyl nitroso-carbamates and boronic acids is reported. The N-nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows for the synthesis of a wide variety of secondary boronates, benzylic boronates and formal Csp3−Csp2 cross-coupling products under operationally simple conditions. Functional group tolerance is also demonstrated and applied in the modification of lysine to make non-canonical amino acids.