Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes

• Published in: Tetrahedron letters Vol. 60; no. 24; pp. 1574 - 1577
• Main Authors: Huang, Pan, Xu, Dawen, Reich, Robert M., Kaiser, Felix, Liu, Boping, Kühn, Fritz E.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 13-06-2019
• Subjects: 1-Alkynes; Alkynylsilanes; C(sp)-H silylation; Et2Zn-mediated; Et2Zn-mediated; C(sp)-H silylation; 1-Alkynes; Alkynylsilanes
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2019.05.017

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•A novel one-step Et2Zn mediated silylation of 1-alkynes and chlorosilanes.•High yields and selectivity as well as well substrate tolerance for this method.•Three possible Zn alkynilide intermediates are proposed.•Complementing the existing zinc-mediated synthesis of alkynylsilanes.•Potentially valuable for organic synthesis.
A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.