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Ir-Catalyzed Asymmetric Hydroarylation of Alkynes for the Synthesis of Axially Chiral Heterobiaryls

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Catal. 2023, 13, 1, 42-48
    Research Article

    Ir-Catalyzed Asymmetric Hydroarylation of Alkynes for the Synthesis of Axially Chiral Heterobiaryls
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    • Pablo Vázquez-Domínguez
      Pablo Vázquez-Domínguez
      Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO−CINQA), Avda. Américo Vespucio, 49, 41092 Seville, Spain
      Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO−CINQA), C/Prof. García González, 1, 41012 Seville, Spain
      More by Pablo Vázquez-Domínguez
    • Antonio Romero-Arenas
      Antonio Romero-Arenas
      Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO−CINQA), Avda. Américo Vespucio, 49, 41092 Seville, Spain
      More by Antonio Romero-Arenas
    • Rosario Fernández*
      Rosario Fernández
      Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO−CINQA), C/Prof. García González, 1, 41012 Seville, Spain
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0002-1755-1525
    • José María Lassaletta*
      José María Lassaletta
      Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO−CINQA), Avda. Américo Vespucio, 49, 41092 Seville, Spain
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0003-1772-2723
    • Abel Ros*
      Abel Ros
      Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO−CINQA), Avda. Américo Vespucio, 49, 41092 Seville, Spain
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0002-3455-5675
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    ACS Catalysis

    Cite this: ACS Catal. 2023, 13, 1, 42–48
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    https://doi.org/10.1021/acscatal.2c04524
    Published December 9, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    The catalytic hydroarylation of alkynes has emerged as an excellent methodology for the synthesis of functionalized alkenes with excellent levels of regio- and stereocontrol (syn). However, in spite of the great progress in this field, the number of asymmetric methodologies is still scarce. Herein, we report an atroposelective Ir-catalyzed C–H hydroarylation of alkynes, which enables the asymmetric synthesis of axially chiral heterobiaryl trisubstituted olefins in good to high yields and enantioselectivities up to 98% ee.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acscatal.2c04524.

    • Experimental details, spectroscopic and analytical data for new compounds, computational details, HPLC traces (PDF)

    • Crystallographic data of (R)-3Ja (CIF)

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    Cited By

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    This article is cited by 9 publications.

    1. Gang Wang, Xinyu Tan, Bing-Xia Yan, Zhe-Wen Zhang, Gen Luo, Zhi-Shi Ye. Palladium-Catalyzed Asymmetric Larock Isoquinoline Synthesis to Access Axially Chiral 3,4-Disubstituted Isoquinolines. Journal of the American Chemical Society 2024, Article ASAP.
    2. Tsuneo Imamoto. P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis. Chemical Reviews 2024, 124 (14) , 8657-8739. https://doi.org/10.1021/acs.chemrev.3c00875
    3. Maoqian Xiong, Zilong Yan, Si-Cong Chen, Jie Tang, Fan Yang, Dong Xing. Iridium-Catalyzed Regiodivergent Atroposelective C–H Alkylation of Heterobiaryls with Alkenes. ACS Catalysis 2024, 14 (9) , 7243-7255. https://doi.org/10.1021/acscatal.4c00519
    4. Hongliang Zhao, Chao-Yue Zhao, Lili Chen, Chungu Xia, Xin Hong, Senmiao Xu. Aryl Chloride-Directed Enantioselective C(sp2)-H Borylation Enabled by Iridium Catalysis. Journal of the American Chemical Society 2023, 145 (46) , 25214-25221. https://doi.org/10.1021/jacs.3c08129
    5. Casey B. Roos, Chang-Hwa Chiang, Lauren A. M. Murray, Di Yang, Luke Schulert, Alison R. H. Narayan. Stereodynamic Strategies to Induce and Enrich Chirality of Atropisomers at a Late Stage. Chemical Reviews 2023, 123 (17) , 10641-10727. https://doi.org/10.1021/acs.chemrev.3c00327
    6. Maoqian Xiong, Feifei Chen, Yuhang Shu, Xiang Wu, Jie Tang, Fan Yang, Dong Xing. Iridium(I)-Catalyzed Atroposelective Alkenylation of Heterobiaryls with Terminal Alkynes. Organic Letters 2023, 25 (31) , 5703-5708. https://doi.org/10.1021/acs.orglett.3c01453
    7. Tatsuhiro Uchikura, Sotaro Kato, Yudai Makino, Megumi J. Fujikawa, Masahiro Yamanaka, Takahiko Akiyama. Chiral Phosphoric Acid–Palladium(II) Complex Catalyzed Asymmetric Desymmetrization of Biaryl Compounds by C(sp3)–H Activation. Journal of the American Chemical Society 2023, 145 (29) , 15906-15911. https://doi.org/10.1021/jacs.3c03552
    8. Sangji Kim, Aram Kim, Chanhee Lee, Junsoo Moon, Eun Jeong Hong, Duck-Hyung Lee, Yongseok Kwon. Atroposelective desymmetrization of 2-arylresorcinols via Tsuji-Trost allylation. Communications Chemistry 2023, 6 (1) https://doi.org/10.1038/s42004-023-00839-z
    9. Qiansujia Zhou, Si-Yong Yin, Dong-Song Zheng, Wen-Wen Zhang, Su-Zhen Zhang, Qing Gu, Shu-Li You. Enantioselective Synthesis of Axially Chiral 1-Arylisoquinolines by Iridium(I)-Catalyzed Hydroarylation of Alkynes. Synlett 2023, 11 https://doi.org/10.1055/a-2021-9514
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    ACS Catalysis

    Cite this: ACS Catal. 2023, 13, 1, 42–48
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.2c04524
    Published December 9, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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