Hydrazine-mediated reduction of nitro and azide functionalities catalyzed by highly active and reusable magnetic iron oxide nanocrystals

Journal of Organic Chemistry

Volumn 78, Issue 9, 2013, Pages 4530-4542

  Cantillo, David ^a   Moghaddam, Mojtaba Mirhosseini ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC NITRO COMPOUNDS; ELEVATED TEMPERATURE; HOMOGENEOUS SOLUTIONS; IRON OXIDE NANOPARTICLE; MAGNETIC IRON OXIDES; MICROWAVE CONDITIONS; QUANTITATIVE YIELDS; REDUCTION OF NITROARENES;

ANILINE; IRON OXIDES; NANOCRYSTALS;

IRON COMPOUNDS;

ANILINE; AROMATIC NITRO COMPOUND; HYDRAZINE; IRON OXIDE; NANOCRYSTAL;

ARTICLE; CATALYSIS; HIGH TEMPERATURE; MICROWAVE RADIATION; QUANTITATIVE ANALYSIS; REDUCTION;

EID: 84877125206     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400556g     Document Type: Article

References (91)

1. Nanoparticles and Catalysis; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
2. Polshettiwar, V.; Varma, R. S. Green Chem. 2010, 12, 743-754
3. Astruc, D.; Lu, F.; Ruiz Aranzaes, J. Angew. Chem., Int. Ed. 2005, 44, 7852-7872
4. Kalidindi, S. B.; Jagirdar, B. R. ChemSusChem 2012, 5, 65-75
5. Zahmakiran, M.; Ozkar, S. Nanoscale 2011, 3, 3462-3481
6. Wang, D. S.; Xie, T.; Li, Y. D. Nano Res. 2009, 2, 30-46
7. Schlogl, R.; Abd Hamid, S. B. Angew. Chem., Int. Ed. 2004, 43, 1628-1637
8. Plietker, B. Iron Catalysis in Organic Chemistry; Wiley-VCH: Wienheim, Germany, 2008.
9. Luque, R.; Baruwati, B.; Varma, R. S. Green Chem. 2010, 12, 1540-1543
10. Zeng, T.; Chen, W.-W.; Cirtiu, C. M.; Moores, A.; Song, G.; Li, C.-J. Green Chem. 2010, 12, 570-573
11. Koukabi, N.; Kolvari, E.; Khazaei, A.; Zolfigol, M. A.; Shirmardi-Shaghasemi, B.; Khavasi, H. R. Chem. Commun. 2011, 47, 9230-9232
12. Yang, C.; Wu, J.; Hou, Y. Chem. Commun. 2011, 47, 5130-5141
13. Shylesh, S.; Schünemann, V.; Thiel, W. R. Angew. Chem., Int. Ed. 2010, 49, 3428-3459
14. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036-3075
15. Nasir, R. B.; Varma, R. S. Chem. Commun. 2013, 49, 752-770
16. Downing, R. S.; Kunkeler, P. J.; van Bekkum, H. Catal. Today 1997, 37, 121-136
17. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
18. Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis; Wiley-Interscience: New York, 2001.
19. Arnold, H.; Döbert, F.; Gaube, J. In Handbook of Heterogeneous Catalysis; Wiley-Interscience: New York, 2008; pp 3266-3284.
20. Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035-2052
21. Corma, A.; Serna, P. Science 2006, 313, 332-334
22. He, L.; Wang, L.-C.; Sun, H.; Ni, J.; Cao, Y.; He, H.-Y.; Fan, K.-N. Angew. Chem., Int. Ed. 2009, 48, 9538-9541
23. Li, M.; Hu, L.; Cao, X.; Hong, H.; Lu, J.; Gu, H. Chem.-Eur. J. 2011, 17, 2763-2768
24. Wu, H.; Zhuo, L.; He, Q.; Liao, X.; Shi, B. Appl. Catal., A 2009, 366, 44-56
25. Amali, A. J.; Rana, R. K. Green Chem. 2009, 11, 1781-1786
26. Li, J.; Shi, X.; Bi, Y.; Wei, J.; Chen, Z. ACS Catal. 2011, 1, 657-664
27. Junge, K.; Wendt, B.; Shaikh, N.; Beller, M. Chem. Commun. 2010, 46, 1769-1771
28. Pehlivan, L.; Métay, E.; Laval, S.; Dayoub, W.; Demonchaux, P.; Mignani, G.; Lemaire, M. Tetrahedron Lett. 2010, 51, 1939-1941
29. Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C. O. M.; Yoon, C. M. Chem. Commun. 2000, 1857-1858
30. Lin, X.; Wu, M.; Wu, D.; Kuga, S.; Endoe, T.; Huang, Y. Green Chem. 2011, 13, 283-287
31. Berthold, H.; Schotten, T.; Hönig, H. Synthesis 2002, 1607-1610
32. Wienhöfer, G.; Sorribes, I.; Boddien, A.; Westerhaus, F.; Junge, K.; Junge, H.; Llusar, R.; Beller, M. J. Am. Chem. Soc. 2011, 133, 12875-12879
33. Sorribes, I.; Wienhöfer, G.; Vicent, C.; Junge, K.; Llusar, R.; Beller, M. Angew. Chem., Int. Ed. 2012, 51, 7794-7798
34. Vass, A.; Dudas, J.; Toth, J.; Varma, R. S. Tetrahedron Lett. 2001, 42, 5347-5349
35. Kumarraja, M.; Pitchumani, K. Appl. Catal. A: Gen. 2004, 265, 135-139
36. Shi, Q.; Lu, R.; Jin, K.; Zhang, Z.; Zhao, D. Green Chem. 2006, 8, 868-870
37. Kim, S.; Kim, E.; Kim, B. M. Chem. Asian J. 2011, 6, 1921-1925
38. Sharma, U.; Verma, P. K.; Kumar, N.; Kumar, V.; Bala, M.; Singh, B. Chem.-Eur. J. 2011, 17, 5903-5907
39. Jagadeesh, R. V.; Wienhöfer, G.; Westerhaus, F. A.; Surkus, A.-E.; Pohl, M.-M.; Junge, H.; Junge, K.; Beller, M. Chem. Commun. 2011, 47, 10972-10974
40. Shi, Q.; Lu, R.; Lu, L.; Fu, X.; Zhao, D. Adv. Synth. Catal. 2007, 349, 1877-1881
41. Luo, P.; Xu, K.; Zhang, R.; Huang, L.; Wang, J.; Xing, W.; Huang, J. Catal. Sci. Technol. 2012, 2, 301-304
42. Cantillo, D.; Baghbanzadeh, M.; Kappe, C. O. Angew. Chem., Int. Ed. 2012, 51, 10190-10193
43. Wiles, C.; Watts, P. Micro Reaction Technology in Organic Synthesis; CRC Press: Boca Raton, FL, 2011.
44. Handbook of Micro Reactors; Hessel, V.; Schouten, J. C.; Renken, A.; Wang, Y.; Yoshida, J.-i., Eds.; Wiley-VCH: Weinheim, 2009.
45. Microreactors in Organic Synthesis and Catalysis; Wirth, T., Ed.; Wiley-VCH: Weinheim, 2008.
46. Wegner, J.; Ceylan, S.; Kirschning, A. Adv. Synth. Catal. 2012, 354, 17-57
47. Wiles, C.; Watts, P. Green Chem. 2012, 14, 38-54
48. Hartman, R. L.; McMullen, J. P.; Jensen, K. F. Angew. Chem., Int. Ed. 2011, 50, 7502-7519
49. Lu, J.; Jiao, X.; Chen, D.; Li, W. J. Phys. Chem. C 2009, 113, 4012-4017
50. Guardia, P.; Labarta, A.; Batlle, X. J. Phys. Chem C. 2011, 115, 390-395
51. Druzhinina, T. S.; Herzer, N.; Hoeppener, S.; Schubert, U. S. ChemPhysChem 2011, 12, 781-784
52. Wiogo, H.; Lim, M.; Munroe, P.; Arnal, R. Cryst. Grown Des. 2011, 11, 1689-1696
53. Iida, H.; Nakanishi, T.; Takada, H.; Osaka, T. Electrochim. Acta 2006, 52, 292-296
54. Wang, W.-W.; Zhu, Y.-J.; Ruan, M.-L. J. Nanopart. Res. 2007, 9, 419-426
55. Osborne, E. A.; Atkins, T. M.; Gilbert, D. A.; Kauzlarich, S. M.; Liu, K.; Louie, A. Y. Nanotechnology 2012, 23, 215602
56. Jia, J.; Yu, J. C.; Zhu, X.-M.; Chan, K. M.; Wang, Y.-X. J. J. Colloid Interface Sci. 2012, 379, 1-7
57. Hayden, S.; Damm, M.; Kappe, C. O. Macromol. Chem. Phys. 2013, 214, 423-434
58. Glasnov, T. N.; Kappe, C. O. Adv. Synth. Catal. 2010, 352, 3089-3097 and references therein
59. Haber, F. Z. Elektrochem. Angew. Phys. Chem. 1898, 22, 506-514
60. Dyson, R. M.; Hazenkamp, M.; Kaufmann, K.; Maeder, M.; Studer, M.; Zilian, A. J. Chemometrics 2000, 14, 737-750
61. Benz, M.; Van der Kraan, A. M.; Prins, R. Appl. Catal., A 1998, 172, 149-157
62. Kumbhar, P. S.; Sanchez-Valente, J.; Millet, J. M. M.; Figueras, F. J. Catal. 2000, 191, 467-473
63. Kumarraja, M.; Pitchumani, K. Appl. Catal., A 2004, 265, 135-139
64. Miller, J. A. Cancer Res. 1970, 3, 559-576
65. Bretherick's Handbook of Reactive Chemical Hazards, 7 th ed.; Urben, P. G., Ed.; Accademic Press: Oxford, 2007.
66. Tong, W. R.; Seagrave, R. L.; Wiederhorn, R. AIChE Loss Prev. 1977, 11, 71-75
67. Siegrist, U.; Baumeister, P.; Blaser, H.-U.; Studer, M. In Catalysis of Organic Reactions; Herkes, F. E., Ed.; Marcel Deker Inc: New York, 1998; pp 207-219.
68. Larsen, J. W.; Freund, M.; Kim, K. Y.; Sidovar, M.; Stuart, J. L. Carbon 2000, 38, 655-661
69. Studer, M.; Neto, S.; Blaser, H.-U. Top. Catal. 2000, 13, 205-212
70. Menga, X.; Chengb, H.; Fujitaa, S.-i.; Haob, Y.; Shangb, Y.; Yu, Y.; Cai, S.; Zhao, F.; Arai, M. J. Catal. 2010, 269, 131-139
71. Cárdenas-Lizana, F.; Gómez-Quero, S.; Keane, M. A. Appl. Catal., A 2008, 334, 199-206
72. Baumeister, P.; Blaser, H.-U.; Studer, M. Catal. Lett. 1997, 49, 219-222
73. Minato, H.; Jujisawa, T. Bull. Chem. Soc. Jpn. 1966, 39, 1054-1058
74. For a review on high-temperature microwave chemistry in water, see: Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563-2591
75. Obermayer, D.; Gutmann, B.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 8321-8324
76. Gutmann, B.; Obermayer, D.; Reichart, B.; Prekodravac, B.; Irfan, M.; Kremsner, J. M.; Kappe, C. O. Chem.-Eur. J. 2010, 16, 12182-12194
77. Kappe, C. O. Acc. Chem. Res. 2013, 10.1021/ar300318c
78. For a recent discussion on microwave effects, see: Kappe, C. O.; Pieber, B.; Dallinger, D. Angew. Chem., Int. Ed. 2013, 52, 1088-1094
79. Lamani, M.; Ravikumara, G. S.; Prabhu, K. R. Adv. Synth. Catal. 2012, 354, 1437-1442
80. Coward, D. M. Neurology 1994, 44, S6-S11
81. Moellering, R. C. Ann. Intern. Med. 2003, 138, 135-142
82. Andersen, J.; Madsen, U.; Björkling, F.; Liang, X. Synlett 2005, 14, 2209-2213
83. Kopach, M. E.; Murray, M. M.; Braden, T. M.; Kobierski, M. E.; Williams, O. L. Org. Process. Res. Dev. 2009, 13, 152-160
84. Malik, A. A.; Preston, S. B.; Archibald, T. G.; Cohen, M. P.; Baum, K. Synthesis 1989, 6, 450-451
85. For an uncatalyzed version providing low selectivity, see: Paterson, T. M.; Smalley, R. K.; Suschitzky, H. Tetrahedron Lett. 1977, 45, 3973-3976
86. Hosseini, M.; Stiasni, N.; Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417-1424
87. O'Brien, M.; Denton, R.; Ley, S. V. Synthesis 2011, 42, 1157-1192
88. Glasnov, T. N.; Kappe, C. O. Chem.-Eur. J. 2011, 17, 11956-11968
89. 4 nanocrystals, see: Simmons, M.; Wiles, C.; Rocher, V.; Francesconi, M. G.; Watts, P. J. Flow Chem. 2013, 3, 7-10 and references cited therein
90. For a detailed description of the Uniqsis FlowSyn set-up, see: Gutmann, B.; Roduit, J.-P.; Roberge, D.; Kappe, C. O. J. Flow Chem. 2012, 2, 8-19
91. Chen, L.; Wang, J.-W.; Hai, L.; Wang, G.-M.; Wu, Y. Synth. Commun. 2010, 40, 789-798