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

Norio Sakai; Nobuaki Takahashi; Daiki Inoda; Reiko Ikeda; Takeo Konakahara

doi:10.3390/molecules181012488

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 Oct 10;18(10):12488-99. doi: 10.3390/molecules181012488.

Authors

Norio Sakai¹, Nobuaki Takahashi, Daiki Inoda, Reiko Ikeda, Takeo Konakahara

Affiliation

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan. sakachem@rs.noda.tus.ac.jp.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetonitriles / chemical synthesis*
Catalysis
Copper / chemistry*
Formaldehyde / chemistry
Methylamines / chemical synthesis*
Models, Chemical
Organometallic Compounds / chemistry*
Polymers / chemistry

Substances

Acetonitriles
Methylamines
Organometallic Compounds
Polymers
copper(II) trifluoromethanesulfonate
Formaldehyde
Copper
cupric chloride
paraform