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Iridium-Catalyzed Enantioselective α-C(sp3)–H Borylation of Azacycles

  • Lili Chen
    Lili Chen
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People’s Republic of China
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    • , 
  • Yuhuan Yang
    Yuhuan Yang
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People’s Republic of China
    University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China
    More by Yuhuan Yang
    • , 
  • Luhua Liu
    Luhua Liu
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People’s Republic of China
    University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China
    More by Luhua Liu
    • , 
  • Qian Gao
    Qian Gao
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People’s Republic of China
    More by Qian Gao
    • , and 
  • Senmiao Xu*
    Senmiao Xu
    State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People’s Republic of China
    Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, People’s Republic of China
    *Email for S.X.: [email protected]
    More by Senmiao Xu
    Orcidhttp://orcid.org/0000-0003-0249-8765
Cite this: J. Am. Chem. Soc. 2020, 142, 28, 12062–12068
Publication Date (Web):June 29, 2020
https://doi.org/10.1021/jacs.0c06756
Copyright © 2020 American Chemical Society
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Abstract

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We herein report an iridium-catalyzed enantioselective α-C(sp3)–H borylation of a wide range of azacycles. The combination of an iridium precursor and a chiral bidentate boryl ligand has been shown to effectively differentiate enantiotropic methylene C–H bonds from a single carbon center, affording a variety of synthetically useful azacycles from readily available starting materials with good to excellent enantioselectivities.

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The Supporting Information is available free of charge on the ACS Publications Web site at DOI: xxxx. (PDF) Crystallographic data of 2aa, 5a, 5k, and S6h. (CIF) The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c06756.

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Cited By

This article is cited by 3 publications.

  1. Łukasz Woźniak, Jin-Fay Tan, Qui-Hien Nguyen, Adrien Madron du Vigné, Vitalii Smal, Yi-Xuan Cao, Nicolai Cramer. Catalytic Enantioselective Functionalizations of C–H Bonds by Chiral Iridium Complexes. Chemical Reviews 2020, 120 (18) , 10516-10543. https://doi.org/10.1021/acs.chemrev.0c00559
  2. Yuhuan Yang, Lili Chen, Senmiao Xu. Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp 3 )–H Borylation of Acyclic Amides. Angewandte Chemie International Edition 2020, 131 https://doi.org/10.1002/anie.202013568
  3. Yuhuan Yang, Lili Chen, Senmiao Xu. Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp 3 )–H Borylation of Acyclic Amides. Angewandte Chemie 2020, 131 https://doi.org/10.1002/ange.202013568

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