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Issue 18, 2014
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Catalytic metal-free Si–N cross-dehydrocoupling

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The metal-free B(C6F5)3 catalyzed dehydrocoupling of hydrosilanes with anilines, carbazoles and indoles is reported. For anilines and carbazoles the reaction proceeds by the liberation of H2 as the sole Si–N coupling byproduct. Indoles react with diphenyl(methyl) hydrosilane to give N-silyl indolines with high diastereoselectivity (d.r. 10 : 1) in excellent yields. A mechanism for this Si–N coupling/hydrogenation sequence is proposed.

Graphical abstract: Catalytic metal-free Si–N cross-dehydrocoupling

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The article was received on 17 Dec 2013, accepted on 10 Jan 2014 and first published on 10 Jan 2014

Article type: Communication
DOI: 10.1039/C3CC49558B
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Citation: Chem. Commun., 2014,50, 2318-2320
  • Open access: Creative Commons BY-NC license
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    Catalytic metal-free Si–N cross-dehydrocoupling

    L. Greb, S. Tamke and J. Paradies, Chem. Commun., 2014, 50, 2318
    DOI: 10.1039/C3CC49558B

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