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

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Abstract

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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Supplementary files

Article information


Submitted
17 Dec 2013
Accepted
10 Jan 2014
First published
10 Jan 2014

This article is Open Access

Chem. Commun., 2014,50, 2318-2320
Article type
Communication
Author version available

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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