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Molecules 2013, 18(10), 12488-12499; doi:10.3390/molecules181012488
Article

Copper-Catalyzed Three- Five- or Seven-Component Coupling Reactions: The Selective Synthesis of Cyanomethylamines, N,N-Bis(Cyanomethyl)Amines and N,N'-Bis(Cyanomethyl)Methylenediamines Based on a Strecker-Type Synthesis

* , , ,  and
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan
* Author to whom correspondence should be addressed.
Received: 28 August 2013 / Revised: 27 September 2013 / Accepted: 27 September 2013 / Published: 10 October 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

We have demonstrated that a cooperative catalytic system comprised of CuCl and Cu(OTf)2 could be used to effectively catalyse the three-, five- and seven-component coupling reactions of aliphatic or aromatic amines, formaldehyde, and trimethylsilyl cyanide (TMSCN), and selectively produce in good yields the corresponding cyanomethylamines, N,N-bis(cyanomethyl)amines and N,N'-bis(cyanomethyl)methylenediamines.
Keywords: multi-component coupling; Strecker-type reaction; nitriles; copper multi-component coupling; Strecker-type reaction; nitriles; copper
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Sakai, N.; Takahashi, N.; Inoda, D.; Ikeda, R.; Konakahara, T. Copper-Catalyzed Three- Five- or Seven-Component Coupling Reactions: The Selective Synthesis of Cyanomethylamines, N,N-Bis(Cyanomethyl)Amines and N,N'-Bis(Cyanomethyl)Methylenediamines Based on a Strecker-Type Synthesis. Molecules 2013, 18, 12488-12499.

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