Are Cu(I)-mesoionic NHC carbenes associated with nitrogen additives the best Cu-carbene catalysts for the azide-alkyne click reaction in solution? A case study

Tetrahedron Letters

Volumn 54, Issue 14, 2013, Pages 1808-1812

  Hohloch, Stephan ^a   Sarkar, Biprajit ^a   Nauton, Lionel ^b,c   Cisnetti, Federico ^b,c   Gautier, Arnaud ^b,c  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

^c ICCF   (France)

Author keywords

Abnormal carbene; Click Chemistry; CuAAC; Mesoionic carbene; N heterocyclic carbene

Indexed keywords

ALKYNE; AMPHOLYTE; AZIDE; CARBENE; CUPROUS ION; NITROGEN; PHENANTHROLINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CLICK CHEMISTRY; CYCLOADDITION; SYNTHESIS;

EID: 84875228872     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.054     Document Type: Article

References (50)

1. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
2. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
3. J. Hou, X. Liu, J. Shen, G. Zhao, and P.G. Wang Expert. Opin. Drug Disc. 7 2012 489 501
4. R.K. Iha, K.L. Wooley, A.M. Nyström, D.J. Burke, M.J. Kade, and C.J. Hawker Chem. Rev. 109 2009 5620 5686
5. D.J. Crowley, and P.H. Bandeen Dalton Trans. 39 2010 612 623
6. Y.H. Lau, P.J. Rutledge, M. Watkinson, and M.H. Tood Chem. Soc. Rev. 40 2011 2848 2866
7. J.D. Crowley, and D. McMorran J. Kosmrlj, Click Triazoles. Topics in Heterocyclic Chemistry Vol. 28 2012 Springer Berlin, Heidelberg 31
8. D. Schweinfurth, F. Weisser, D. Bubrin, L. Bogani, and B. Sarkar Inorg. Chem. 50 2011 6114 6121
9. D. Schweinfurth, S. Demeshko, M.M. Khusniyarov, S. Dechert, V. Gurram, M.R. Buchmeiser, F. Meyer, and B. Sarkar Inorg. Chem. 51 2012 7592 7597
10. C.W. Tornøe, and M. Meldal Peptides: The Wave of the Future 2001 Kluwer Academic Dordrecht
11. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
12. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952 3015
13. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302 1315
14. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207 4220
15. For TBTA, see: T.R. Chan, R. Hilgraf, K.B. Sharpless, and V.V. Fokin Org. Lett. 6 2004 2853 2855
16. A. Maisonial, O. Serafin, M. Traïkia, E. Debiton, V. Théry, D.J. Aitken, P. Lemoine, B. Viossat, and A. Gautier Eur. J. Inorg. Chem. 2008 298 305
17. V. Hong, S.I. Presolski, C. Ma, and M.G. Finn Angew. Chem., Int. Ed. 48 2009 9879 9883
18. For bathophenanthroline, see: W.G. Lewis, F.G. Magallon, V.V. Fokin, and M.G. Finn J. Am. Chem. Soc. 126 2004 9152 9153
19. For a general review, see: S. Díez-González Catal. Sci. Technol. 1 2011 166 178
20. For N-Ligand, see: N. Candelon, D. Lastécouères, A. Khadri Diallo, J. Ruiz Aranzaes, D. Astruc, and J.-M. Vincent Chem. Commun. 2008 741 743
21. S. Özçubukçu, E. Ozkal, C. Jimeno, and M.A. Pericàs Org. Lett. 11 2009 4680 4683
22. F. Li, and T.S.A. Hor Chem. Eur. J. 15 2009 10585 10592
23. For P ligand, see: F. Pérez-Balderas, M. Ortega-Muñoz, J. Morales-Sanfrutos, F. Hernández-Mateo, F.G. Calvo-Flores, J.A. Calvo-Asín, J. Isac-García, and F. Santoyo-González Org. Lett. 5 2003 1951 1954
24. S. Lal, J. McNally, A.J.P. White, and S. Díez-González Organometallics 30 2011 6225 6235
25. For C-ligand (excluding NHCs): M. Liu, and O. Reiser Org. Lett. 13 2011 1102 1105
26. For S-ligand see: P. Fabbrizzi, S. Cicchi, A. Brandi, E. Sperotto, and G. van Koten Eur. J. Org. Chem. 2009 5423 5430
27. For review, see: J.D. Crowley, A.-L. Lee, and K.J. Kilpin Aust. J. Chem. 64 2011 1118 1132
28. D. Martin, M. Melaimi, M. Soleilhavoup, and G. Bertrand Organometallics 30 2011 5304 5313
29. O. Schuster, L. Yang, H.G. Raubenheimer, and M. Albrecht Chem. Rev. 109 2009 3445 3478
30. For NHCs, see: S. Díez-González, A. Correa, L. Cavallo, and S.P. Nolan Chem. Eur. J. 12 2006 7558 7564
31. S. Díez-González, and S.P. Nolan Angew. Chem., Int. Ed. 47 2008 8881 8884
32. S. Díez-González, E.D. Stevens, and S.P. Nolan Chem. Commun. 2008 4747 4749
33. S. Díez-González, E.C. Escudero-Adán, J. Benet-Buchholz, E.D. Stevens, A.M.Z. Slawin, and S.P. Nolan Dalton Trans. 39 2010 7595 7606
34. J. Broggi, S. Díez-González, J.L. Petersen, S. Berteina-Raboin, S.P. Nolan, and L.A. Agrofoglio Synthesis 2008 141 148
35. W. Wang, J. Wu, C. Xia, and F. Li Green Chem. 13 2011 3440 3445
36. M.-L. Teyssot, A. Chevry, M. Traikia, M. El-Ghozzi, D. Avignant, and A. Gautier Chem. Eur. J. 15 2009 6322 6326
37. M.-L. Teyssot, L. Nauton, J.-L. Canet, F. Cisnetti, A. Chevry, and A. Gautier Eur. J. Org. Chem. 2010 3507 3515
38. C. Gaulier, A. Hospital, B. Legeret, A.F. Delmas, V. Aucagne, F. Cisnetti, and A. Gautier Chem. Commun. 48 2012 4005 4007
39. B. Letribot, R. Akué-Gédu, N.M. Santio, M. El-Ghozzi, D. Avignan, F. Cisnetti, P.J. Koskinen, A. Gautier, F. Anizon, and P. Moreau Eur. J. Med. Chem. 2012 304 310
40. Z. Chamas, X. Guo, J.-L. Canet, A. Gautier, D. Boyer, and R. Mahiou Dalton Trans. 39 2010 7091 7097
41. For mesoionic NHCs, see: T. Nakamura, T. Terashima, K. Ogata, and S.-I. Fukuzawa Org. Lett. 13 2011 620 632
42. S. Hohloch, C.-Y. Su, and B. Sarkar Eur. J. Inorg. Chem. 2011 3067 3075
43. P. Mathew, A. Neels, and M. Albrecht J. Am. Chem. Soc. 130 2008 13534 13535
44. For gaussian 09: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B., et al. gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford CT, 2009.
45. For basis set exchange: M.N. Glukhovstev, A. Pross, M.P. McGrath, and L. Radom J. Chem. Phys. 103 1995 1878 1885
46. D. Feller J. Comput. Chem. 17 1996 1571 1586
47. K.L. Schuchardt, B.T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, and T.L. Windus J. Chem. Inf. Model. 47 2007 1045 1052 This methodology has proven to be successful for complex 10 as the calculated structure is in very good agreement with the X-ray one (see Refs. 6h,j, respectively)
48. A. Poater, B. Cosenza, A. Correa, S. Giudice, F. Ragone, V. Scarano, and L. Cavallo Eur. J. Inorg. Chem. 2009 1759 1766
49. V.A. Krylova, P.I. Djurovich, M.T. Whited, and M.E. Thompson Chem. Commun. 46 2010 6696 6698
50. The X-ray structure of a copper(I)-triazolide is reported in the literature, see: C. Nolte, P. Mayer, and B.F. Straub Angew. Chem., Int. Ed. 46 2007 2101 2103