Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: <i>N</i><sup>2</sup>-Selective Alkylation of Benzotriazole
作者:Kenzo Yahata、Yuki Kaneko、Shuji Akai
DOI:10.1021/acs.orglett.9b04375
日期:2020.1.17
transfer from a catalytically generated cobalt(III)-hydride complex to the olefins proceeded regioselectively, and the nucleophilic addition of benzotriazoles occurred selectively at their N2-positions. The syntheticutility of the obtained N2-alkylated benzotriazoles as stable amine protecting groups under various reaction conditions was demonstrated, and the products were also transformed into primary
Attachment of carbonyl functionalities onto olefins via copper-promoted radical reaction of dichloromethylcyanides
作者:Shin Kamijo、Shinya Yokosaka、Masayuki Inoue
DOI:10.1016/j.tet.2012.01.089
日期:2012.7
Chemo- and regioselective protocols for attachment of various carbonyl functionalities onto unactivated olefins have been developed. Atom transfer radical reactions of Cl3CCN, Cl2C(R)CN, and Cl2C(CN)2 were all promoted efficiently by a catalytic amount of CuCl and 1,1′-bis(diphenylphosphino)ferrocene to introduce chloromethylcyanide and chloride units to the C–Cdoublebonds. Conversion of the chloromethylcyanide
Cobalt-Catalyzed Hydroamination of Alkenes with 5-Substituted Tetrazoles: Facile Access to 2,5-Disubstituted Tetrazoles and Asymmetric Intermolecular Hydroaminations
作者:Kenzo Yahata、Yuki Kaneko、Shuji Akai
DOI:10.1248/cpb.c20-00068
日期:2020.4.1
Herein, we describe a novel synthetic method for 2,5-disubstituted tetrazoles from 5-substituted tetrazoles using cobalt-catalyzed intermolecular hydroamination reaction of nonactivated olefins. Owing to its mild conditions, the method enabled the use of substrates having acid-labile functional groups, such as silyloxy and methoxymethyloxy groups. By using optically active cobalt complexes, asymmetric