A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water

Tetrahedron Letters

Volumn 52, Issue 52, 2011, Pages 7171-7174

  Teo, Yong Chua ^a   Yong, Fui Fong ^a   Lim, Gina Shiyun ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

Bimetallic; Copper; Coupling; Manganese; N arylation

Indexed keywords

1,2 DIAMINOCYCLOHEXANE; COPPER; HALIDE; HETEROCYCLIC NITRO COMPOUND; IMIDAZOLE; INDAZOLE DERIVATIVE; INDOLE; MANGANESE; NITROGEN; NUCLEOPHILE; PYRAZOLE; PYRROLE; WATER;

ARTICLE; ARYLATION; CATALYST; CROSS COUPLING REACTION; REACTION OPTIMIZATION;

EID: 82255183225     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.128     Document Type: Article

References (58)

1. V. Ritleng, C. Sirlin, and M. Pfeffer Chem. Rev. 102 2002 1731
2. A.R. Muci, and S.L. Buchwald Top. Curr. Chem. 219 2002 131
3. F. Diederich, and A. Meijere Metal-Catalyzed Cross-Coupling Reactions 2004 Wiley-VCH Weinheim
4. L.-C. Campeau, and K. Fagnou Chem. Commun. 2005 1253
5. O. Daugulis, V.G. Zaitsev, D. Shabashou, Q.-N. Pham, and A. Lazareva Synlett 2006 3382
6. K. Godula, and S. Sames Science 312 2006 67
7. A.R. Dick, and M.S. Sanford Tetrahedron 62 2006 2439
8. J.F. Hartwig Synlett 2006 1283
9. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174
10. I.V. Seregin, and V. Gevorgyan Chem. Soc. Rev. 36 2007 1173
11. H.M.L. Davies, and J.R. Manning Nature 451 2008 417
12. J.B. Buckingham Dictionary of Natural Products 1994 CRC Press Vol. 1
13. Y. Oshiro, S. Sato, N. Kurahashi, T. Tanaka, T. Kikuchi, K. Tottori, Y. Uwahodo, and T. Nishi J. Med. Chem. 41 1998 658
14. A.J. Belfield, G.R. Brown, and A.J. Foubister Tetrahedron 55 1999 11399
15. S.A. Lawrence Amines Synthesis Properties and Application 2004 Cambridge University Press Cambridge
16. F. Ullmann Ber. Deutsch. Chem. Ges. 36 1903 2382
17. For a review, see: M. Schnürcg, R. Flasik, A.F. Khan, M. Spina, M.D. Mihovilovic, and P. Stanetty Eur. J. Org. Chem. 2006 3283
18. P.-F. Larsson, A. Correa, M. Carril, P.-O. Norrby, and C. Bolm Angew. Chem., Int. Ed. 48 2009 5691
19. Reviews: S.V. Ley, and A.W. Thomas Angew. Chem. Int. Ed. 42 2003 5400
20. K. Kunz, U. Scholtz, and D. Ganzer Synlett 2003 2428
21. I.P. Beletskaya, and A.V. Cheprakov Coord. Chem. Rev. 248 2004 2337
22. J.-P. Corbert, and G. Mignani Chem. Rev. 106 2006 2651
23. For diamines as the ligands in Cu-catalysed C-N coupling, see: A. Klapars, J.C. Antila, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7727
24. J.C. Antila, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 11684
25. A. Klapars, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 7421
26. J.C. Antila, J.M. Baskin, T.E. Barder, and S.L. Buchwald J. Org. Chem. 69 2004 5578
27. R.K. Rao, A.B. Naidu, E.A. Jaseer, and G. Sekar Tetrahedron 65 2009 4619
28. For diols as the ligands in Cu-catalysed C-N coupling, see: F.Y. Kwong, A. Klapars, and S.L. Buchwald Org. Lett. 4 2002 581
29. G.E. Job, and S.L. Buchwald Org. Lett. 4 2002 3703
30. D. Jiang, H. Fu, Y. Jiang, and Y. Zhao J. Org. Chem. 72 2007 672
31. For amino acids and amino alcohols as the ligands in Cu-catalysed C-N coupling, see: D. Ma, Y. Zhang, J. Yao, S. Wu, and F. Tao J. Am. Chem. Soc. 120 1998 12459
32. D. Ma, and C. Xia Org. Lett. 3 2001 2583
33. D. Ma, Q. Cai, and H. Zhang Org. Lett. 5 2003 2453
34. Z. Wang, W. Bao, and Y. Jiang Chem. Commun. 2005 2849
35. Z. Lu, and R.J. Twieg Tetrahedron 61 2005 903
36. Q. Cai, W. Zhu, H. Zhang, Y. Zhang, and D. Ma Synthesis 2005 496
37. H. Zhang, Q. Cai, and D. Ma J. Org. Chem. 70 2005 5164
38. J. Kim, and S. Chang Chem. Commun. 2008 3052
39. For oxime phosphines as the ligands in Cu-catalysed C-N coupling, see: L. Xu, J. Mao, D. Zhu, F. Wu, R. Wang, and B. Wan Tetrahedron 61 2006 6553
40. D. Zhu, L. Xu, F. Wu, and B. Wan Tetrahedron Lett. 47 2006 5781
41. For salicylaldoximes as the ligands in Cu-catalysed C-N coupling, see: F.Y. Kwong, and S.L. Buchwald Org. Lett. 5 2003 793
42. H.-J. Cristau, P.P. Cellier, J.-F. Spindler, and M. Taillefer Chem. Eur. J. 10 2004 5607
43. H.-J. Cristau, P.P. Cellier, J.-F. Spindler, and M. Taillefer Eur. J. Org. Chem. 2004 695
44. Q. Jiang, D. Jiang, Y. Jiang, H. Fu, and Y. Zhao Synlett 2007 1836
45. For β-diketones and β-keto esters as the ligands in Cu-catalysed C-N coupling, see: A. Shafir, and S.L. Buchwald J. Am. Chem. Soc. 128 2006 8742
46. B. de Lange, M.H. Lambers-Verstappen, L.S. de Vondervoort, N. Sereinig, R. de Rijk, A.H.M. de Vries, and J.G. de Vries Synlett 2006 3105
47. A. Shafir, P.A. Lichtor, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 3490
48. X. Lv, and W. Bao J. Org. Chem. 72 2007 3863
49. N. Xia, and M. Taillefer Angew. Chem., Int. Ed. 48 2009 337
50. D. Wang, and K. Ding Chem. Commun. 2009 1891
51. M. Taillefer, N. Xia, and A. Ouali Angew. Chem., Int. Ed. 46 2007 934
52. Z. Wang, H. Fu, Y. Jiang, and Y. Zhao Synlett 2008 2540
53. D. Guo, H. Huang, Y. Zhou, J. Xu, H. Jiang, K. Chen, and H. Liu Green Chem. 12 2010 276
54. P.A. Grieco Organic Synthesis in Water 1998 Blackie Academic & Professional London
55. U.M. Lindstrom Chem. Rev. 102 2002 2751
56. C.J. Li Chem. Rev. 105 2005 3095
57. D. Sinou Adv. Synth. Catal. 344 2002 221
58. Y.-C. Teo, F.-F. Yong, C.-Y. Poh, Y.-K. Yan, and G.-L. Chua Chem. Commun. 2009 6258