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Iridium-Catalyzed γ-Selective Hydroboration of γ-Substituted Allylic Amides

  • Hongliang Zhao
    Hongliang Zhao
    Green Catalysis Center, College of Chemistry, Henan Advanced Institute of Technology, Zhengzhou University, Zhengzhou 450001, China
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, China
  • Qian Gao
    Qian Gao
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, China
    More by Qian Gao
  • Yajuan Zhang
    Yajuan Zhang
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, China
    More by Yajuan Zhang
  • Panke Zhang*
    Panke Zhang
    Green Catalysis Center, College of Chemistry, Henan Advanced Institute of Technology, Zhengzhou University, Zhengzhou 450001, China
    *Email: [email protected]
    More by Panke Zhang
  • , and 
  • Senmiao Xu*
    Senmiao Xu
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, China
    Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China
    University of Chinese Academy of Sciences, Beijing 100049, China
    *Email: [email protected]
    More by Senmiao Xu
Cite this: Org. Lett. 2020, 22, 7, 2861–2866
Publication Date (Web):March 23, 2020
https://doi.org/10.1021/acs.orglett.0c00977
Copyright © 2020 American Chemical Society
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Abstract

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Reported here for the first time is the Ir-catalyzed γ-selective hydroboration of γ-substituted allylic amides under mild reaction conditions. A variety of functional groups could be compatible with reaction conditions, affording γ-branched amides in good yields with ≤97% γ-selectivity. We have also demonstrated that the obtained borylated products could be used in a series of C–O, C–F, C–Br, and C–C bond-forming reactions.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.0c00977.

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Cited By


This article is cited by 1 publications.

  1. Dongseong Park, Doohyun Baek, Chi-Woo Lee, Huijeong Ryu, Seungchul Park, Woosong Han, Sukwon Hong. Enantioselective C(sp2)–H borylation of diarylmethylsilanes catalyzed by chiral pyridine-dihydroisoquinoline iridium complexes. Tetrahedron 2021, 79 , 131811. https://doi.org/10.1016/j.tet.2020.131811

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