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Mannich reactions of alkynes: mechanistic insights and the role of sub-stoichiometric amounts of alkynylcopper(I) compounds in the catalytic cycle

journal contribution
posted on 06.01.2015, 16:54 by Benjamin BuckleyBenjamin Buckley, Amna N. Khan, Harry Heaney
Yellow polymeric alkynylcopper(I) compounds observed in the three-component Mannich reactions of alkynes, secondary amines and aldehydes are shown to be pre-catalysts that give rise to catalytic copper(I) alkyne complexes by interaction with secondary amines (see scheme). Interaction of these complexes with iminium ions (formed from aldehydes or their equivalents, including CH2Cl2), results in the formation of Mannich bases in high yields.

Funding

The authors are grateful to The Higher Education Commission of Pakistan and Loughborough University for research funding. B. R. B. also thanks Research Councils UK for a RCUK fellowship.

History

School

  • Science

Department

  • Chemistry

Published in

CHEMISTRY-A EUROPEAN JOURNAL

Volume

18

Issue

13

Pages

3855 - 3858 (4)

Citation

BUCKLEY, B.R., KHAN, A.N. and HEANEY, H., 2012. Mannich reactions of alkynes: mechanistic insights and the role of sub-stoichiometric amounts of alkynylcopper(I) compounds in the catalytic cycle. Chemistry - A European Journal, 18 (13), pp. 3855 - 3858.

Publisher

© Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2012

Notes

This article is closed access.

ISSN

0947-6539

Language

en