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Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst

  • Jia-Le Wang
    Jia-Le Wang
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
    More by Jia-Le Wang
  • Guan-Yu Wu
    Guan-Yu Wu
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
    More by Guan-Yu Wu
  • Jian-Nan Luo
    Jian-Nan Luo
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
    More by Jian-Nan Luo
  • Jun-Long Liu
    Jun-Long Liu
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
    More by Jun-Long Liu
  • , and 
  • Chun-Xiang Zhuo*
    Chun-Xiang Zhuo
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China
    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
    *Email: [email protected]
Cite this: J. Am. Chem. Soc. 2024, 146, 8, 5605–5613
Publication Date (Web):February 13, 2024
https://doi.org/10.1021/jacs.3c14195
Copyright © 2024 American Chemical Society

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    Abstract

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    Carbonyl is highly accessible and acts as an essential functional group in chemical synthesis. However, the direct catalytic deoxygenative functionalization of carbonyl compounds via a putative metal carbene intermediate is a formidable challenge due to the requirement of a high activation energy for the cleavage of strong C═O double bonds. Here, we report a class of bench stable and readily available Cp*Mo(II)-complexes as efficient deoxygenation catalysts that could catalyze the direct intermolecular deoxygenative coupling of carbonyl compounds with alkynes. Enabled by this powerful Cp*Mo(II)-catalyst, various valuable heteroarenes (10 different classes) were obtained in generally good yields and remarkable chemo- and regioselectivities. Mechanistic studies suggested that this reaction might proceed via a sequence of C═O double bonds cleavage, carbene-alkyne metathesis, cyclization, and aromatization processes. This strategy not only provided a general catalytic platform for the rapid preparation of heteroarenes but also opened a new window for the applications of Cp*Mo(II)-catalysts in organic synthesis.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.3c14195.

    • Experimental procedures, characterizations and analytical data of products, and NMR spectra (PDF)

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    CCDC 23074492307454 contain the supplementary crystallographic datafor 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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