Issue 3, 2015
From the journal:

Green Chemistry

Synthesis of tetrasubstituted propargylamines from cyclohexanone by solvent-free copper(ii) catalysis†

Zachary L. Palchak,a   Daniel J. Lussier,a   Conor J. Piercea  and  Catharine H. Larsen*a  

* Corresponding authors

a Department of Chemistry, University of California, Riverside, CA 92521, USA
E-mail: catharine.larsen@ucr.edu
Tel: (+1)-951-827-4964

Abstract

Copper(II) chloride catalyzes the three-component coupling of cyclohexanone, amines, and alkynes to produce tetrasubstituted propargylamines. As a wide range of substrates react without solvent, excess starting material, or other additives, water is the sole by-product. Studies demonstrate that this reaction is first order in copper, cyclohexanone, amine, and alkyne. These mild conditions allow for the first direct, catalytic synthesis of silyl-protected tetrasubstituted propargylamines.

Graphical abstract: Synthesis of tetrasubstituted propargylamines from cyclohexanone by solvent-free copper(ii) catalysis

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Article information

DOI
https://doi.org/10.1039/C4GC02318H
Article type
Paper
Submitted
24 Nov 2014
Accepted
13 Jan 2015
First published
13 Jan 2015

Green Chem., 2015,17, 1802-1810

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Synthesis of tetrasubstituted propargylamines from cyclohexanone by solvent-free copper(II) catalysis

Z. L. Palchak, D. J. Lussier, C. J. Pierce and C. H. Larsen, Green Chem., 2015, 17, 1802 DOI: 10.1039/C4GC02318H

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