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Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis

Abstract : A completely regioselective and challenging gold(I)-catalyzed ring-opening of cyclic 1,3-dioxolanes and dioxanes by trimethylsilyl alkynes to set diol-derived propargyl trimethylsilyl bis-ethers is reported. This unprecedented and not trivial transformation does not operate with the catalytic methodologies recently reported for catalytic alkynylation of acyclic acetals/ketals, and is uniquely enabled by the application of a recently introduced synergistic gold(I)-silicon catalysis concept capable of producing simultaneously catalytic amounts of two key players, a silicon-based Lewis superacid and a nucleophilic gold acetylide. © 2017 American Chemical Society.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413280
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Submitted on : Monday, December 16, 2019 - 10:43:23 AM
Last modification on : Friday, December 20, 2019 - 1:10:57 PM

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M. Berthet, O. Songis, C. Taillier, V. Dalla. Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (18), pp.9916-9922. ⟨10.1021/acs.joc.7b01828⟩. ⟨hal-02413280⟩

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