Synlett 2013; 24(10): 1190-1192
DOI: 10.1055/s-0033-1338944
cluster
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene (NHC)–Copper(I) Complexes as Catalysts for A3 Reactions

Ming-Tsz Chen
,
Oscar Navarro*
Further Information

Publication History

Received: 04 March 2013

Accepted after revision: 19 April 2013

Publication Date:
10 May 2013 (online)


Abstract

The use of easily synthesized NHC–Cu(I) complexes for the preparation of a variety of propargylamines through an A3 ­coupling scheme is described.

Supporting Information

 
  • References and Notes

  • 1 Current address: Department of Chemistry, University of Sussex, Brighton, BN1 9QJ, UK.
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  • 15 Representative Example: 1-(1-Cyclohexyl-3-phenyl-2-propynyl)piperidine (4) 1H NMR (300 MHz, CDCl3): δ = 0.89–1.11 (m, 2 H), 1.15–1.35 (m, 3 H), 1.45–1.50 (m, 2 H), 1.57–1.72 (m, 6 H), 1.78–1.82 (m, 2 H), 2.05–2.17 (m, 2 H), 2.40–2.46 (m, 2 H), 2.63–2.70 (m, 2 H), 3.13 (d, J = 9.9 Hz, 1 H), 7.29–7.35 (m, 3 H), 7.45–7.48 (m, 2 H). 13C{1H} NMR (75 MHz, CDCl3): δ = 26.7, 26.1, 26.3, 26.8, 30.4, 31.3, 39.6, 64.3, 86.1, 87.7, 123.8, 127.5, 128.1, 131.7.