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A Water-Soluble Rhenium(I) Catalyst for the Regio- and Stereoselective C(sp2)–H Alkenylation of N-Pyridyl-/N-Pyrimidylindole and the N–H Alkenylation of N-Pyrimidylaniline Derivatives with Ynamides

  • Sundaramoorthi Sarathkumar
    Sundaramoorthi Sarathkumar
    Department of Chemistry, National Taiwan Normal University, No-88, Sec.4, Ting- Zhou Road, Taipei 11677, Taiwan R.O.C.
  • Veerababurao Kavala
    Veerababurao Kavala
    Department of Chemistry, National Taiwan Normal University, No-88, Sec.4, Ting- Zhou Road, Taipei 11677, Taiwan R.O.C.
  • , and 
  • Ching- Fa Yao*
    Ching- Fa Yao
    Department of Chemistry, National Taiwan Normal University, No-88, Sec.4, Ting- Zhou Road, Taipei 11677, Taiwan R.O.C.
    *E-mail: [email protected]
Cite this: Org. Lett. 2021, 23, 6, 1960–1965
Publication Date (Web):February 1, 2021
https://doi.org/10.1021/acs.orglett.0c04068
Copyright © 2021 American Chemical Society

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    Abstract

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    A water-soluble and low-valent rhenium(I) catalyst for the C2 alkenylation of N-pyridyl/N-pyrimidylindole derivatives with ynamides under mild conditions using water as the solvent has been described. The reaction of N-pyridyl/N-pyrimidyl indole with the ynamide afforded the C2-Z-selective alkenylation derivative as the sole product, and the reactions of N-pyrimidylanilines delivered the corresponding N-alkenylated product rather than the expected C–H alkenylation products in high yields under the same conditions.

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    CCDC 20479292047932 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

    This article is cited by 7 publications.

    1. Jivan Shinde, Veerababurao Kavala, Ching-Fa Yao. Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one. Organic Letters 2023, 25 (38) , 6943-6948. https://doi.org/10.1021/acs.orglett.3c02192
    2. Yuanshuang Xu, Caiyun Yu, Xinying Zhang, Xuesen Fan. Synthesis of Indolyl-Tethered Spiro[cyclobutane-1,1′-indenes] through Cascade Reactions of 1-(Pyridin-2-yl)-1H-indoles with Alkynyl Cyclobutanols. Organic Letters 2021, 23 (21) , 8510-8515. https://doi.org/10.1021/acs.orglett.1c03200
    3. Irena Roterman, Katarzyna Stapor, Leszek Konieczny. Ab initio protein structure prediction: the necessary presence of external force field as it is delivered by Hsp40 chaperone. BMC Bioinformatics 2023, 24 (1) https://doi.org/10.1186/s12859-023-05545-0
    4. Tariq A. Shah, Tanumay Sarkar, Subhradeep Kar, Prabhat Kumar Maharana, Kangkan Talukdar, Tharmalingam Punniyamurthy. Transition‐Metal‐Catalyzed Directed C−H Functionalization in/on Water. Chemistry – An Asian Journal 2023, 50 https://doi.org/10.1002/asia.202300815
    5. Yongli Zhao, Yongliang Tu, Mingzhong Cai, Junfeng Zhao. Recent Advances in the Synthesis of Ynamides. Chinese Journal of Organic Chemistry 2022, 42 (1) , 85. https://doi.org/10.6023/cjoc202107051
    6. Yanru Wang, Zhen Zhao, Songkui Lv, Lixia Ding, Xiao-Na Wang, Junbiao Chang. Nonmetal-catalyzed hydroamination of ynamides with amines. Organic Chemistry Frontiers 2021, 8 (22) , 6244-6251. https://doi.org/10.1039/D1QO01052B
    7. Jiaxu Tang, Yuhai Tang, Xiaonan Wang, Yongzhuang Wang, Xiaoli Huang, Silong Xu, Yang Li. Regioselective cascade annulation of indoles with alkynediones for construction of functionalized tetrahydrocarbazoles triggered by Cp*Rh III -catalyzed C–H activation. Organic Chemistry Frontiers 2021, 8 (14) , 3809-3814. https://doi.org/10.1039/D1QO00616A

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