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Rhodium-Catalyzed Atroposelective C–H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2019, 141, 24, 9504-9510
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    Rhodium-Catalyzed Atroposelective C–H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls
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    • Qiang Wang
      Qiang Wang
      State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Qiang Wang
    • Zhong-Jian Cai
      Zhong-Jian Cai
      State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Zhong-Jian Cai
    • Chen-Xu Liu
      Chen-Xu Liu
      State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Chen-Xu Liu
    • Qing Gu
      Qing Gu
      State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      More by Qing Gu
      Orcidhttp://orcid.org/0000-0003-4963-2271
    • Shu-Li You*
      Shu-Li You
      State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
      *[email protected]
      More by Shu-Li You
      Orcidhttp://orcid.org/0000-0003-4586-8359
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    Cite this: J. Am. Chem. Soc. 2019, 141, 24, 9504–9510
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    https://doi.org/10.1021/jacs.9b03862
    Published June 2, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Rhodium(I)-catalyzed atroposelective C–H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)2Cl]2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C–H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.

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    This article is cited by 168 publications.

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    Cite this: J. Am. Chem. Soc. 2019, 141, 24, 9504–9510
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