A convenient and general ruthenium-catalyzed transfer hydrogenation of nitro- and azobenzenes

Chemistry - A European Journal

Volumn 17, Issue 51, 2011, Pages 14375-14379

  Jagadeesh, Rajenahally V ^a   Wienhöfer, Gerrit ^a   Westerhaus, Felix A ^a   Surkus, Annette Enrica ^a   Junge, Henrik ^a   Junge, Kathrin ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

anilines; azo compounds; hydrogenation; propanol; ruthenium

Indexed keywords

AZO COMPOUND; IN-SITU; P-CYMENE; SELECTIVE TRANSFER; TERPYRIDINES; TRANSFER HYDROGENATIONS;

ANILINE; HYDROGENATION; PROPANOL; RUTHENIUM; RUTHENIUM COMPOUNDS;

CATALYST SELECTIVITY;

4-CYMENE; ANILINE DERIVATIVE; AZO COMPOUND; NITROBENZENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PARA CYMENE; RUTHENIUM; TERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; SYNTHESIS;

ANILINE COMPOUNDS; AZO COMPOUNDS; CATALYSIS; HYDROGENATION; MOLECULAR STRUCTURE; MONOTERPENES; NITROBENZENES; ORGANOMETALLIC COMPOUNDS; RUTHENIUM;

EID: 83755183658     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102276     Document Type: Article

References (75)

1. R. S. Downing, P. J. Kunkeler, H. van Bekkum, Catal. Today 1997, 37, 121-136
2. N. Ono, The Nitro Group in Organic Synthesis Wiley-VCH, New York, 2001.
3. 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, pp. 389-406
4. S. Nishimura, Handbook of Heterogeneous Hydrogenation of Organic Synthesis, Wiley, New York, 2001
5. N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, 170-177
6. N. J. Jebarathinam, M. Eswaramoorthy, V. Krishnasamy, in Recent Advances in Basic and Applied Aspects of Industrial Catalysis (Eds.:, T. S. R. P. Rao and G. M. Dhar,), Elsevier Science 1998, 1039-1043.
7. M. Takasaki, Y. Motoyama, K. Higashi, S. H. Yoon, I. Mochida, H. Nagashima, Org. Lett. 2008, 10, 1601-1604
8. A. Corma, C. G. Arellano, M. Iglesias, F. Sánchez, Appl. Catal. A 2009, 356, 99-102
9. F. Cárdenas-Lizana, S. Gõmez-Quero, M. A. Keane, Catal. Commun. 2008, 9, 475-481
10. Y. Chen, J. Qiu, X. Wang, J. Xiu, J. Catal. 2006, 242, 227-230
11. H. Wua, L. Zhuo, Q. He, X. Liao, B. Shi, Appl. Catal. A-Gen. 2009, 366, 44-56
12. J. Wang, Z. Yuan, R. Nie, Z. Hou, X. Zheng, Ind. Eng. Chem. Res. 2010, 49, 4664-4669
13. H. U. Blaser, Science 2006, 313, 312
14. A. Corma, P. Serna, P. Concepcion, J. Calvino, J. Am. Chem. Soc. 2008, 130, 8748-8753
15. M. L. Kantam, R. Chakravarti, U. Pal, B. Sreedhar, S. Bhargava, Adv. Synth. Catal. 2008, 350, 822-827
16. G. Y. Fan, L. Zhang, H-Y. Fu, M. L. Yuan, R. X. Li, H. Chen, X. J. Li, Catal. Commun. 2010, 11, 451-455.
17. J. W. Bae, Y. J. Cho, S. H. Lee, C. O. M. Yoon, C. M. Yoon, Chem. Commun. 2000, 1857-1858
18. J. W. Bae, Y. J. Cho, S. H. Lee, C. M. Yoon, Tetrahedron Lett. 2000, 41, 175-177.
19. K. Junge, B. Wendt, N. Shaikh, M. Beller, Chem. Commun. 2010, 46, 1769-1771
20. R. J. Rahaim, R. E. Maleczka, Org. Lett. 2005, 7, 5087-5090.
21. C. T. Redemann, C. E. Redemann, Org. Synth. 1955, 3, 69.
22. U. Sharma, P. Kumar, N. Kumar, V. Kumar, B. Singh, Adv. Synth. Catal. 2010, 352, 1834-1840
23. M. Lauwiner, P. Rys, J. Wissmann, Appl. Catal. A-Gen. 1998, 172, 141-148
24. T. M. Jyothi, R. Rajagopal, K. Sreekumar, M. B. Talawar, S. Sugunan, B. S. Rao, J. Chem. Res-S 1999, 674-675
25. D. H. Lloyd, D. E. Nichols, J. Org. Chem. 1986, 51, 4294-4295.
26. H. Imai, T. Nishiguchi, K. Fukuzumi, Chem. Lett. 1976, 655-656
27. H. Berthold, T. Schotten, H. Hönig, Synthesis 2002, 1607-1610.
28. S. Gowda, K. Abiraj, D. C. Gowda, Tetrahedron Lett. 2002, 43, 1329-1331
29. K. Abiraj, Srinivasa, R. Gejjalagere, D. C. Gowda, Can. J. Chem. 2005, 83, 517-520.
30. S. Gladiali, G. Mestroni, in Transition Metals for Organic Synthesis (Eds.:, M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2004
31. S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226-236
32. J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237-248
33. G. Brieger, T. J. Nestrick, Chem. Rev. 1974, 74, 567-580.
34. S. Enthaler, B. Hagemann, G. Erre, K. Junge, M. Beller, Chem. Asian J. 2006, 1, 598-604
35. S. Zhou, S. Fleischer, K. Junge, S. Das, D. Addis, M. Beller, Angew. Chem. 2010, 122, 8298-8302
36. Angew. Chem. Int. Ed. 2010, 49, 8121-8125
37. S. Enthaler, B. Spilker, G. Erre, K. Junge, M. K. Tse, M. Beller, Tetrahedron 2008, 64, 3867-3876
38. M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett. 2007, 9, 2791-2793
39. J. F. Bower, R. L. Patman, M. J. Krische, Org Lett. 2008, 10, 1033-1035
40. F. Alonso, P. Riente, M. Yus, Synlett 2008, 1289-1292
41. F. Alonso, P. Riente, M. Yus, Tetrahedron 2009, 65, 10637-10643.
42. Q. Peng, Y. Zhang, F. Shi, Y. Deng, Chem. Commun. 2011, 47, 6476-6478
43. X. Cui, Y. Zhang, F. Shi, Y. Deng, Chem. Eur. J. 2011, 17, 2587-2591.
44. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, P. Selvam, Tetrahedron Lett. 2002, 43, 8527-8529
45. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, P. Selvam, Appl. Catal. B-Environ. 2003, 46, 155-163
46. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, P. Selvam, Org. Lett. 2002, 4, 4297-4230
47. S. U. Sonavane, S. K. Mohapatra, R. V. Jayaram, P. Selvam, Chem. Lett. 2003, 32, 142-143
48. A. S. Kulkarni, R. V. Jayaram, J. Mol. Catal. A-Chem. 2004, 223, 107-110
49. A. S. Kulkarni, R. V. Jayaram, Appl. Catal. A-Gen. 2003, 252, 225-230
50. S. U. Sonavane, M. B. Gawand, S. S. Deshpande, A. Venkataraman, R. V. Jayaram, Catal. Commun. 2007, 8, 1803-1806.
51. V. Z. Sharf, L. K. Freidlin, B. M. Savchenko, V. N. Krutii, Russ. Chem. Bull. 1979, 28, 1061-1063.
52. G. K. Jnaneshwara, A. Sudalai, V. H. Deshpande, J. Chem. Res-S 1998, 160-161
53. A. Mobinikhaledi, N. Foroughifar, H. F. Jirandehi, Monatsh. Chem. 2007, 138, 755-757
54. F. Alonso, G. Radivoy, M. Yus, Tetrahedron 2000, 56, 8673-8678
55. P. Selvama, S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, Appl. Catal. B-Environ. 2004, 49, 251-255.
56. I. Jovel, S. Prateeptongkum, R. Jackstell, N. Vogel, C. Weckbecker, M. Beller, Chem. Commun. 2010, 46, 1956-1958
57. S. Imm, S. Bähn, A. Tillack, K. Mevius, L. Neubert, M. Beller, Chem. Eur. J. 2010, 16, 2705-2709
58. S. Bähn, S. Imm, K. Mevius, L. Neubert, A. Tillack, J. M. J. Williams, M. Beller, Chem. Eur. J. 2010, 16, 3590-3593
59. G. Wienhöfer, K. Schröder, K. Möller, K. Junge, M. Beller, Adv. Synth. Catal. 2010, 352, 1615-1620
60. S. Imm, S. Bähn, L. Neubert, H. Neumann, M. Beller, Angew. Chem. 2010, 122, 8303-8306
61. Angew. Chem. Int. Ed. 2010, 49, 8126-8129
62. C. Federsel, R. Jackstell, A. Boddien, G. Laurenczy, M. Beller, ChemSusChem 2010, 3, 1048-1050
63. W. Mägerlein, C. Dreisbach, H. Hugl, M. K. Tse, M. Klawonn, S. Bhor, M. Beller, Catal. Today 2007, 121, 140-150
64. D. Hollmann, A. Tillack, D. Michalik, R. Jackstell, M. Beller, Chem. Asian J. 2007, 2, 403-410
65. S. Enthaler, K. Junge, D. Addis, G. Erre, M. Beller, ChemSusChem 2008, 1, 1006-1010.
66. S. Enthaler, B. Hagemann, G. Erre, K. Junge, M. Beller, Adv. Synth. Catal. 2007, 349, 853-860
67. S. Enthaler, R. Jackstell, A. Zapf, B. Hagemann, G. Erre, K. Junge, M. Beller, J. Organomet. Chem. 2006, 691, 4652-4659
68. M. Zhao, Z. Yu, S. Yan, Y. Li, Tetrahedron Lett. 2009, 50, 4624-4628
69. W. Baratta, P. Rigo, Eur. J. Inorg. Chem. 2008, 4041-4053
70. N. A. Cortez, G. Aguirre, M. Parra-Hake, R. Somanathan, Tetrahedron: Asymmetry 2008, 19, 1304-1309
71. W. Baratta, K. Siega, P. Rigo, Adv. Synth. Catal. 2007, 349, 1633-1636
72. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522
73. J. Takehara, S. Hashiguchi, A. Fujii, S. Inoue, T. Ikariya, R. Noyori, Chem. Commun. 1996, 233-234
74. D. Xue, Y-C. Chen, X. Cui, Q-W. Wang, J. Zhu, J.-G. Deng, J. Org. Chem. 2005, 70, 3584-3591.
75. A. Aranyos, G. Csjernyik, K. J. Szabõ, J.-E. Bäckvall, Chem. Commun. 1999, 351-352.