Selective catalytic hydrogenation of functionalized nitroarenes: An update

ChemCatChem

Volumn 1, Issue 2, 2009, Pages 210-221

  Blaser, Hans Ulrich ^a   Steiner, Heinz ^a   Studer, Martin ^a,b  

^a SOLVIAS AG   (Switzerland)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Chemoselectivity; Heterogeneous catalysis; Hydrogenation; Reduction; Supported catalysts

Indexed keywords

BENZYL GROUP; CARBON CARBONS; CATALYTIC SYSTEM; CHEMO-SELECTIVITY; FUNCTIONALIZED; HOMOGENEOUS CATALYST; MECHANISTIC ASPECTS; SELECTIVE CATALYTIC HYDROGENATIONS;

CATALYSIS; CATALYST SUPPORTS; HYDROGENATION; REDUCTION;

CATALYSTS;

EID: 76749162502     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.200900129     Document Type: Review

References (72)

1. A. M. Strätz, Chem. Ind. (Dekker) 1984, 18, 335.
2. R. S. Downing, P. J. Kunkeler, H. van Bekkum, Catal. Today 1997, 37, 121.
3. For a recent overview on synthetic aspects of the catalytic reduction of nitroarenes, see: H. U. Blaser, U. Siegrist, H. Steiner, M. Studer, in Fine Chemicals through Heterogeneous Catalysis (Eds.: R. A. Sheldon, H. van Bekkum), Wiley-VCH, Weinheim, 2001, p. 389.
4. For an extensive overview on the older literature see: a) Houben-Weyl, Methoden der Organischen Chemie, Thieme Verlag Stuttgart, 4/1c, 1980, pp. 511-532;
5. b) Houben-Weyl, Methoden der Organischen Chemie, Thieme Verlag Stuttgart, 4/1c, 1980, p. 531.
6. For a recent review see: X. Wang, M. Liang, J. Zhang, Y. Wang, Current Organic Chemistry 2007, 11, 299.
7. For an account see: P. Baumeister, H. U. Blaser, U. Siegrist, M. Studer, Chem. Ind. (Dekker) 1998, 75, 207 and references therein.
8. R. Braden, H. Knupfer, S. Hartung, U.S. Pat. 4 002673 and 4 051177 (1977, Bayer AG).
9. A. Onopchenko, E. T. Sabourin, C. M. Selwitz, J. Org. Chem. 1979, 44, 1233.
10. S. Nishimura, Handbook of Heterogeneous Hydrogenation of Organic Synthesis Wiley, New York, 2001, p. 350.
11. P. Baumeister, H. U. Blaser, M. Studer, Catal. Lett. 1997, 49, 219.
12. P. Baumeister, H. U. Blaser, W. Scherrer, Stud. Surf. Sci. Catal. 1991, 59, 321 and references therein.
13. Commercial catalysts: a) E. Auer, A. Freund, M. Gross, R. Hartung, P. Panster, Chem. Ind. (Dekker) 1998, 75, 551;
14. b) G. G. Ferrier, F. King, Platinum Met. Rev. 1983, 27, 72.
15. G. Wu, M. Huang, M. Richards, M. Poirier, X. Wen, R. W. Draper, Synthesis 2003, 1657.
16. X. Han, R. Zhou, X. Zheng, H. Jiang, J. Mol. Catal. A 2003, 193, 103.
17. W. Tu, H. Liu, Y. Tang, J. Mol. Catal. A 2000, 159, 115.
18. X. Han, R. Zhou, G. Lai, B. Yue, X. Zheng, J. Mol. Catal. A 2004, 209, 83.
19. H. S. Wilkinson, R. Hett, G. J. Tanoury, C. H. Senanayake, S. A. Wald, Org. Process Res. Dev. 2000, 4, 567.
20. H. Sajiki, K. Hattori, K. Hirota, J. Org. Chem. 1998, 63, 7990.
21. A. Mori, T. Mizusaki, M. Kawase, T. Maegawa, Y. Monguchi, S. Takao, Y. Takagi, H. Sajiki, Adv. Synth. Catal. 2008, 350, 406.
22. J. M. Hawkins, T. W. Makowski, Org. Process Res. Dev. 2001, 5, 328.
23. A. Akao, K. Sato, N. Nonoyama, T. Mase, N. Yasuda, Tetrahedron Lett. 2006, 47, 969.
24. S. Ichikawa, M. Tada, Y. Iwasawa, T. Ikariya, Chem. Commun. 2005, 924.
25. D.-Q. Xu, Z.-Y. Hu, W.-W. Li, S.-P. Luo, Z.-Y. Xu, J. Mol. Catal. A 2005, 235, 137.
26. B. Coq, A. Tijani, F. Figueras, J. Mol. Catal. A 1991, 68, 331.
27. B. Coq, A. Tijani, R. Dutartre, F. Figueras, J. Mol. Catal. A 1993, 79, 253.
28. H. Bönnemann, W. Wittholt, J. D. Jentsch, A. S. Tilling, New J. Chem. 1998, 22, 713.
29. C. Liu, Z. Zhou, Z. Wu, M. Fransson, B. Zhou, Synlett 2009, 595.
30. A. Corma, P. Serna, P. Conception, J. J. Calvino, J. Am. Chem. Soc. 2008, 130, 8748.
31. M. Takasaki, Y. Motoyama, K Higashi, S-H. Yoon, I. Mochida, H. Nagashima, Org. Lett. 2008, 10, 1601.
32. J. Zhang, Y. Wang, H. Ji, Y. Wei, Y. Wu, B. Zuo, Q. Wang, J. Catal. 2005, 229, 114.
33. F. Wang, J. Liu, X. Xu, Chem. Commun. 2008, 2040.
34. J. Xiong, J. Chen, J. Zhang, Catal. Commun. 2007, 8, 345.
35. N. Mahata, A. F. Cunha, J. J. M. Orfao, J. L. Figueiredo, Catal. Commun. 2009, 10, 1203.
36. B. Zuo, Y. Wang, Q. Wang, J. Zhang, J. Wu, L. Peng, L. Gui, X. Wang, R. Wang, D. Yu, J. Catal. 2004, 222, 493.
37. F. Cardenas-Lizana, S. Gomez-Quero, M. A. Keane, J. Mol. Catal. A 2008, 334, 199.
38. For an overview see P. Claus, Appl. Catal. A 2005, 291, 222.
39. Y. Chen, C. Wang, H. Liu, J. Qiu, X. Bao, Chem. Commun. 2005, 5298.
40. A. Corma, P. Serna, Science 2006, 313, 332.
41. For a comment see: H. U. Blaser, Science 2006, 313, 312.
42. a) Y. Chen, J. Qiu, X. Wang, J. Xiu, J. Catal. 2006, 242, 227;
43. b) D. He, H. Shi, Y. Wu B-Q. Xu, Green Chem. 2007, 9, 849-851.
44. F. Cárdenas-Lizana, S. Gomez-Quero, M. A. Keane, Catal. Commun. 2008, 9, 475.
45. F. Cárdenas-Lizana, S. Gomez-Quero, M. A. Keane, ChemSusChem 2008, 1, 215.
46. F. Cárdenas-Lizana, S. Gomez-Quero, A. Hugon, L. Delannoy, C. Louis, M. A. Keane, J. Catal. 2009, 262, 235.
47. F. Cárdenas-Lizana, S. Gomez-Quero, M. A. Keane, Catal. Lett. 2009, 127, 25.
48. A. Corma, C. Gonzales-Arellano, M. Iglesias, F. Sanchez, Appl. Catal. A 2009, 356, 99.
49. X. Liu, S. Lu, J. Mol. Catal. A 2009, 300, 36.
50. X. Liu, S. Lu, J. Mol. Catal. A 2004, 212, 127.
51. L. Liu, B. Qiao, Z. Chen, J. Zhang, Y. Deng, Chem. Commun. 2009, 653.
52. M. Lauwiner, P. Rys, J. Wissmann, Appl. Catal. A 1998, 172, 141;
53. M. Lauwiner, R. Roth, P. Rys, J. Wissmann, Stud. Surf. Sci. Catal. 1997, 108, 231.
54. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, P. Selvam, Org. Lett. 2002, 4, 4297.
55. R. J. Rahaim, R. E. Maleczka, Org. Lett. 2005, 7, 5087.
56. P. M. Reis, B. Royo, Tetrahedron Lett. 2009, 50, 949.
57. H-Y. Lee, M. Aun, Bull. Korean Chem. Soc. 2004, 25, 1717.
58. J. Spencer, N. Anjum, H. Patel, R. P. Rathnam, J. Verma, Synlett 2007, 2557.
59. F. Li, J. Cu, X. Qian, R. Zhang, Chem. Commun. 2004, 2338.
60. H. Steiner, Solvias AG, unpublished laboratory experiments.
61. T. J. N. Watson, S. W. Horgan, R. S. Shah, R. A. Farr, R. A. Schnettler, C. R. Nevill, F. J. Weiberth, E. W. Huber, B. M. Baron, M. E. Webster, R. K. Mishra, B. L. Harrison, P. L. Nyce, C. L. Rand, C. T. Goralski, Org. Process Res. Dev. 2000, 4, 477.
62. J. Hou, Y. Ma, Y. Li, F. Guo, L. Lu, Chem. Lett. 2008, 37, 974.
63. F. Haber, Z. Elektrochem. Angew. Phys. Chem. 1898, 22, 506;
64. R. M. Dyson, M. Hazenkamp, K. Kaufmann, M. Maeder, M. Studer, A. Zilian, J. Chemom. 2000, 14, 737.
65. F. Visentin, G. Puxty, O. Kut, K. Hungerbuehler, Ind. Eng. Chem. Res. 2006, 45, 4544.
66. a) E. A. Gelder, S. D. Jackson, C. M. Lok, Chem. Commun. 2005, 522;
67. b) E. A. Gelder, S. D. Jackson, C. M. Lok, Chem. Ind. (Dekker) 2007, 115, 522.
68. a) A. Corma, P. Concepcion, P. Serna, Angew. Chem. 2007, 119, 7404;
69. Angew. Chem. Int. Ed. 2007, 46, 7266;
70. b) M. Boronat, P. Concepcion, A. Corma, S. Gonzalez, F. Illas, P. Serna, J. Am. Chem. Soc. 2007, 129, 16230.
71. I. A. Makaryan, V. I. Savchenko, Stud. Surf. Sci. Catal. 1993, 75, 2439.
72. M. Boronat, F. Illas, A. Corma, J. Phys. Chem. A 2009, 113, 3750.