Short synthesis of bis-NHC-Pd catalyst derived from caffeine and its applications to Suzuki, Heck, and Sonogashira reactions in aqueous solution

Journal of Organometallic Chemistry

Volumn 696, Issue 6, 2011, Pages 1262-1265

  Luo, Fen Tair ^a   Lo, Hung Kun ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

bis NHC Pd complex; Caffeine; Heck reaction; NHC; Sonogashira reaction; Suzuki reaction

Indexed keywords

CAFFEINE; HECK REACTION; NHC; PD COMPLEX; SONOGASHIRA REACTIONS; SUZUKI REACTION;

CATALYST SUPPORTS; PALLADIUM COMPOUNDS; SOLUTIONS;

SYNTHESIS (CHEMICAL);

EID: 79952362217     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.11.002     Document Type: Conference Paper

References (55)

1. B.L. Oliveira, and O.A.C. Antunes Lett. Org. Chem. 4 2007 13
2. H.-J. Yoon, S.-M. Lee, J.-H. Kim, and Y.-S. Lee Appl. Chem. 10 2006 517
3. R.K. Arvela, and N.E. Leadbeater J. Org. Chem. 70 2005 161
4. A. Alimardanov, L. Schmieder-van de Vodervoort, A.H.M. de Vries, and J.G. de Vries Adv. Synth. Catal. 346 2004 1812
5. E. Peris, and R.H. Crabtree Coord. Chem. Rev. 248 2004 2239
6. C.M. Crudden, and D.P. Allen Coord. Chem. Rev. 248 2004 2247
7. N.E. Leadbeater, and M. Marco Org. Lett. 4 2002 2973
8. W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1290
9. D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand Chem. Rev. 100 2000 39
10. J. Schwarz, V.P.W. Böhm, M.G. Gardiner, M. Grosche, W.A. Herrmann, W. Hieringer, and G. Raudaschl-Sieber Chem. Eur. J. 6 2000 1773
11. T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, and W.A. Herrmann Angew. Chem. Int. Ed. 38 1999 2416
12. W.A. Herrmann, K. Öfele, M. Elison, F.E. Kühn, and P.W. Roesky J. Organomet. Chem. 480 1994 C7
13. K. Öfele, W.A. Herrmann, D. Mihalios, M. Elison, E. Herdtweck, and W. Scherer J. Organomet. Chem. 459 1993 177
14. F.E. Hahn, and M.C. Jahnke Angew. Chem. Int. Ed. 47 2008 3122
15. A.T. Normand, and K.J. Cavell Eur. J. Inorg. Chem. 2008 2781
16. S.T. Liddle, I.S. Edworthy, and P.L. Arnold Chem. Soc. Rev. 36 2007 1732
17. D. Enders, O. Niemeier, and A. Henseler Chem. Rev. 107 2007 5606
18. N. Marion, S. Díez-González, and S.P. Nolan Angew. Chem. Int. Ed. 46 2007 2988
19. F. Glorius Top. Organomet. Chem. 21 2007 1
20. O. Kühl Chem. Soc. Rev. 36 2007 592
21. S.P. Nolan, N-heterocyclic carbenes in synthesis 2006 Wiley-VCH Weinheim, Germany
22. R.H. Crabtree J. Organomet. Chem. 689 2005 5451
23. A.J. Arduengo, R.L. Harlow, and M. Kilne J. Am. Chem. Soc. 113 1991 361
24. A. Poater, F. Ragone, S. Giudice, C. Costabile, R. Dorta, S.P. Nolan, and P. Cavallo Organometallics 27 2008 2679
25. E. Peris Top. Organomet. Chem. 21 2007 83
26. R. Corberán, J. Ramírez, M. Poyatos, E. Perisa, and E. Fernández Tetrahedron: Asymmetry 17 2006 1759
27. W. Wei, Y. Qin, M. Luo, P. Xia, and M.S. Wong Organometallics 27 2008 2268
28. M.G. Organ, M. Abdel-Hadi, S. Avola, I. Dubovyk, N. Hadei, E.A.B. Kantchev, C.J. O"Brien, M. Sayah, and C. Valente Chem. Eur. J. 14 2008 2443
29. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem. Int. Ed. 46 2007 2768
30. S. Díez-González, and S.P. Nolan Top. Organomet. Chem. 21 2007 47
31. N. Marion, O. Navarro, J. Mei, E.D. Stevens, N.M. Scott, and S.P. Nolan J. Am. Chem. Soc. 128 2006 4101
32. J.C.Y. Lin, R.T.W. Huang, C.S. Lee, A. Bhattacharyya, W.S. Hwang, and I.J.B. Lin Chem. Rev. 109 2009 3561
33. C.J. O'Brien, E.A.B. Kantchev, C. Valente, N. Hadei, G.A. Chass, A. Lough, A.C. Hopkinson, and M.G. Organ Chem. Eur. J. 12 2006 4743
34. E.E. Hahn, M.C. Jahnke, V. Gomez-Beitez, D. Morales-Morales, and T. Pape Organometallics 24 2005 6458
35. W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1290
36. J.A. Loch, M. Albrecht, E. Peris, J. Mata, J.W. Faller, and R.H. Crabtree Organometallics 21 2002 700
37. L. Bai, J.X. Wang, and Y. Zhang Green Chem. 5 2003 615
38. M. Nüchter, B. Ondruschka, W. Bonrath, and A. Gum Green Chem. 6 2004 128
39. V. Pironti, and S. Colonna Green Chem. 7 2005 43
40. N.E. Leadbeater Chem. Commun. 2005 2881
41. C.G. Blettner, W.A. König, W. Stenzel, and T. Schotten J. Org. Chem. 64 1999 3885
42. D. Villemin, M.J. Gómez-Escalonilla, and J.-F. Saint-Clair Tetrahedron Lett. 42 2001 635
43. W. Solodenko, U. Schön, J. Messinger, A. Glinschert, and A. Kirschning Synlett 2004 1699
44. M.D. Crozet, C. Castera-Ducros, and P. Vanelle Tetrahedron Lett. 47 2006 7061
45. K.H. Shaughnessy Eur. J. Org. Chem. 71 2006 1827
46. R. Franzén, and Y. Xu Can. J. Chem. 83 2005 266
47. L.R. Moore, and K.H. Shaughnessy Org. Lett. 6 2004 225
48. K.W. Anderson, and S.L. Buchwald Angew. Chem. Int. Ed. 44 2005 6173
49. H. J-Li, C. X-Hu, Y. Liang, and Y.-X. Xie Tetrahedron 62 2006 31
50. E.J.G. Suárez, A. Ruiz, S. Castillón, W. Oberhauser, C. Bianchini, and C.J. Claver J. Chem. Soc. Dalton Trans. 2007 2859
51. C.A. Quezada, J.C. Garrison, M.J. Panzner, C.A. Tessier, and W.J. Youngs Organometallics 23 2004 4846
52. A. Kascatan-Nebioglu, M.J. Panzner, J.C. Garrison, C.A. Tessier, and W.J. Youngs Organometallics 23 2004 1928
53. J. Schuetz, and W.A. Herrmann J. Organomet. Chem. 689 2004 2995
54. A. Kascatan-Nebioglu, A. Melaiye, K. Hindi, S. Durmus, M.J. Panzner, L.A. Hogue, R.J. Mallett, C.E. Hovis, M. Coughenour, S.D. Crosby, A. Milsted, D.L. Ely, C.A. Tessier, C.L. Cannon, and W.J. Youngs J. Med. Chem. 49 2006 6811
55. A. Krasovskiy, C. Duplais, and B.H. Lipshutz J. Am. Chem. Soc. 131 2009 15592