Biogenous iron oxide-immobilized palladium catalyst for the solvent-free Suzuki-Miyaura coupling reaction

Tetrahedron Letters

Volumn 53, Issue 3, 2012, Pages 329-332

  Mandai, Kyoko ^a   Korenaga, Toshinobu ^a   Ema, Tadashi ^a   Sakai, Takashi ^a   Furutani, Mitsuaki ^a   Hashimoto, Hideki ^a   Takada, Jun ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Biogenous iron oxide; Immobilized catalyst; Palladium catalyst; Solvent free reaction; Suzuki Miyaura coupling reaction

Indexed keywords

IMIDAZOLE DERIVATIVE; IMIDAZOLIUM CHLORIDE; IRON OXIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; LEPTOTHRIX; LEPTOTHRIX OCHRACEA; MIYAURA REACTION; NONHUMAN; SUZUKI REACTION;

LEPTOTHRIX OCHRACEA;

EID: 83555173483     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.044     Document Type: Article

References (46)

1. H. Hashimoto, S. Yokoyama, H. Asaoka, Y. Kusano, Y. Ikeda, M. Seno, J. Takada, T. Fujii, M. Nakanishi, and R. Murakami J. Magn. Magn. Mater. 310 2007 2405
2. T. Ema, Y. Miyazaki, I. Kozuki, T. Sakai, H. Hashimoto, and J. Takada Green Chem. 13 2011 3187
3. T. Sakai, Y. Miyazaki, A. Murakami, N. Sakamoto, T. Ema, H. Hashimoto, M. Furutani, M. Nakanishi, T. Fujii, and J. Takada Org. Biomol. Chem. 8 2010 336
4. J. Tsuji Palladium Reagents and Catalysts New Perspective for the 21st Century 2004 Wiley England
5. For a recent example, see: S. Kawamorita, H. Ohmiya, T. Iwai, and M. Sawamura Angew. Chem., Int. Ed. 50 2011 8363
6. For reviews on the Suzuki-Miyaura coupling reacions, see: S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
7. A. Suzuki J. Organomet. Chem. 576 1999 147
8. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
9. For recent reviews, see: Á. Molnár Chem. Rev. 111 2011 2251
10. M. Lamblin, L. Nassar-Hardy, J.-C. Hierso, E. Fouquet, and F.-X. Felpin Adv. Synth. Catal. 352 2010 33
11. F. Alonso, I.P. Beletskaya, and M. Yus Tetrahedron 64 2008 3047
12. L. Yin, and J. Liebscher Chem. Rev. 107 2007 133
13. N.T.S. Phan, M.V.D. Sluys, and C.W. Jones Adv. Synth. Catal. 348 2006 609
14. For recent reviews, see: N. Marion, and S.P. Nolan Acc. Chem. Res. 41 2008 1440
15. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem., Int. Ed. 46 2007 2768
16. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Aldrichim. Acta 39 2006 97
17. Without TBAB, the reaction did not proceed sufficiently. For the enhancement of Suzuki-Miaura cross coupling reaction in water by TBAB, see: C. Schmöger, T. Szuppa, A. Tied, F. Schneider, A. Stolle, and B. Ondruschka ChemSusChem 1 2008 339
18. D. Badone, M. Baroni, R. Cardamone, A. Ielmini, and U. Guzzi J. Org. Chem. 62 1997 7170
19. For recent examples on silica-supported palladium catalysts for the Suzuki-Miyaura coupling reactions, see: N. Fukuya, M. Ueda, S. Onozawa, K.K. Bando, T. Miyaji, Y. Takagi, T. Sakakura, and H. Yasuda J. Mol. Catal. A: Chem. 342-343 2011 58
20. W. Chen, P. Li, and L. Wang Tetrahedron 67 2011 318
21. H. Yang, X. Han, G. Li, Z. Ma, and Y. Hao J. Phys. Chem. C 114 2010 22221
22. X. Feng, M. Yan, T. Zhang, Y. Liu, and M. Bao Green Chem. 12 2010 1758
23. The products 3a-h were identified by comparison with the spectroscopic data in the literatures: For 3a, 3b, 3e, 3f, 3g, see: R. Bandari, T. Höche, A. Prager, K. Dirnberger, and M.R. Buchmeiser Chem. Eur. J. 16 2010 4650
24. For 3c, see: C.E. Hartmann, S.P. Nolan, and C.S.J. Cazin Organometallics 28 2009 2915
25. For 3d, see: M. Döbele, S. Vanderheiden, N. Jung, and S. Bräse Angew. Chem., Int. Ed. 49 2010 5986
26. For the solvent-free Suzuki-Miyaura coupling reactions with solid-supported palladium catalysts, see: D. Braga, D. D'Addario, and M. Polito Organometallics 23 2004 2810
27. B. Basu, P. Das, Md.M.H. Bhuiyan, and S. Jha Tetrahedron Lett. 44 2003 3817
28. G.W. Kabalka, L. Wang, R.M. Pagni, C.M. Hair, and V. Namboodri Synthesis 2003 217
29. M. Melucci, G. Barbarella, and G. Sotgiu J. Org. Chem. 67 2002 8877
30. D. Villemin, and F. Caillot Tetrahedron Lett. 42 2001 639
31. G.W. Kabalka, R.M. Pagni, L. Wang, V. Namboodiri, and C.M. Hair Green Chem. 2 2000 120
32. G.W. Kabalka, R.M. Pagni, and C.M. Hair Org. Lett. 1 1999 1423
33. For the solvent-free Suzuki-Miyaura coupling reactions with nonimmobilized palladium catalysts, see: J.-H. Li, C.-L. Deng, and Y.-X. Xie Synth. Commun. 37 2007 2433
34. L.M. Klingensmith, and N.E. Leadbeater Tetrahedron Lett. 44 2003 765
35. N. Linares, A.E. Sepúlveda, M.C. Pacheco, J.R. Berenguer, E. Lalinde, C. Nájera, and J. Garcia-Martinez New J. Chem. 35 2011 225
36. F. Bernhardt, R. Trotzki, T. Szuppa, A. Stolle, and B. Ondruschka Beilstein J. Org. Chem. 2010 6 No. 7
37. P. Nun, J. Martinez, and F. Lamaty Synlett 2009 1761
38. L. Tao, Y. Xie, C. Deng, and J. Li Chin. J. Chem. 27 2009 1365
39. F. Schneider, T. Szuppa, A. Stolle, B. Ondruschka, and H. Hopf Green Chem. 11 2009 1894
40. F. Schneider, A. Stolle, B. Ondruschka, and H. Hopf Org. Process Res. Dev. 13 2009 44
41. W. Chang, J. Shin, Y. Oh, and B.J. Ahn J. Ind. Eng. Chem. 14 2008 423
42. F. Schneider, and B. Ondruschka ChemSusChem 1 2008 622
43. V. Kogan, Z. Aizenshtat, R. Popovitz-Biro, and R. Neumann Org. Lett. 4 2002 3529
44. S.F. Nielsen, D. Peters, and O. Axelsson Synth. Commun. 30 2000 3501
45. L. Djakovitch, K. Köhler, and J.G. de Vries The Role of Palladium Nanoparticles as Catalysts for Carbon-Carbon Coupling Reactions D. Astruc, Nanoparicles and Catalysis first ed. 2008 Wiley-VCH Weinheim, Germany 303
46. K. Okumura, H. Matsui, T. Sanada, M. Arao, T. Honma, S. Hirayama, and M. Niwa J. Catal. 265 2009 89