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.
  • 2 Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005

    • Some recent reviews on MCR:
    • 3a Ruitjer E, Scheffelaar R, Orru RV. A. Angew. Chem. Int. Ed. 2011; 50: 6234
    • 3b Ganem B. Acc. Chem. Res. 2009; 42: 463
    • 3c Ramón DJ, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
  • 4 Yoo W.-J, Zhao L, Li C.-J. Aldrichimica Acta 2011; 44: 43
    • 5a Meyet CE, Pierce CJ, Larsen CH. Org. Lett. 2012; 4: 964
    • 5b Shi L, Tu Y.-Q, Wang M, Zhang F.-M, Fan C.-A. Org. Lett. 2004; 6: 1001
  • 6 Nakamura S, Ohara M, Nakamura Y, Shibata N, Toru T. Chem. Eur. J. 2010; 16: 2360
  • 7 Bisai A, Singh VA. Org. Lett. 2006; 8: 2405
  • 8 Knöpfel TF, Aschwanden P, Ichikawa T, Watanabe T, Carreira EM. Angew. Chem. Int. Ed. 2004; 43: 5971
  • 10 Wang M, Li P, Wang L. Eur. J. Org. Chem. 2008; 2255
  • 11 Chen M.-T, Landers B, Navarro O. Org. Biomol. Chem. 2012; 10: 2206
  • 12 Landers B, Navarro O. Eur. J. Inorg. Chem. 2012; 2980
  • 13 Citadelle CA, Nouy EL, Bisaro F, Slawin AM. Z. Dalton Trans. 2010; 39: 4489
  • 14 Li Y, Chen X, Song Y, Fanf L, Zou G. Dalton Trans. 2011; 40: 2046
  • 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.