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Stereoselective Synthesis of Z-Vinylsilanes via Palladium-Catalyzed Direct Intermolecular Silylation of C(sp2)–H Bonds

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    Stereoselective Synthesis of Z-Vinylsilanes via Palladium-Catalyzed Direct Intermolecular Silylation of C(sp2)–H Bonds
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    † ‡ †School of Chemistry and Chemical Engineering, ‡Key Laboratory for Thin Film and Microfabrication of Ministry of Education, and §Zhiyuan College, Shanghai Jiao Tong University, Shanghai 200240, People’s Republic of China
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 19, 5216–5219
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    https://doi.org/10.1021/acs.orglett.7b02486
    Published September 21, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    An efficient and convenient palladium-catalyzed direct intermolecular silylation of C(sp2)–H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b02486.

    • Experimental procedures, NMR spectra, and X-ray and analytical data for all new compounds (PDF)

    • X-ray data for compound 3aa (CIF)

    • X-ray data for compound 3ba (CIF)

    • X-ray data for compound 1t-int (CIF)

    • X-ray data for compound 11 (CIF)

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 19, 5216–5219
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b02486
    Published September 21, 2017
    Copyright © 2017 American Chemical Society
    Request reuse permissions

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