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

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(10):12488-12499.

Chicago/Turabian Style

Sakai, Norio; Takahashi, Nobuaki; Inoda, Daiki; Ikeda, Reiko; Konakahara, Takeo. 2013. "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 18, no. 10: 12488-12499.

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