Iron-catalyzed synthesis of secondary amines: On the way to green reductive aminations

ChemSusChem

Volumn 7, Issue 11, 2014, Pages 3012-3016

  Stemmler, Tobias ^a   Surkus, Annette Enrika ^a   Pohl, Marga Martina ^a   Junge, Kathrin ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Heterogeneous catalysis; Hydrogenation; Iron; Nitroarenes; Reductive amination

Indexed keywords

ALDEHYDES; AMINATION; AMINES; CARBON; CATALYSIS; CATALYSTS; CONDENSATION REACTIONS; HYDROGENATION; IRON;

CATALYZED SYNTHESIS; CHEMICAL AND BIOLOGICALS; IRON-BASED CATALYST; IRON-PHENANTHROLINE COMPLEXES; NITROARENES; REACTION SEQUENCES; REDUCTIVE AMINATION; SECONDARY AMINES;

IRON COMPOUNDS;

ALDEHYDE; AMINE; CARBON; IMINE; IRON; NANOMATERIAL; NITRO DERIVATIVE;

AMINATION; CATALYSIS; CHEMISTRY; GREEN CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; AMINATION; AMINES; CARBON; CATALYSIS; GREEN CHEMISTRY TECHNOLOGY; IMINES; IRON; NANOSTRUCTURES; NITRO COMPOUNDS; OXIDATION-REDUCTION;

EID: 84925860704     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201402413     Document Type: Article

References (68)

1. C. A. Buehler, D. E. Pearson, Survey of Organic Synthesis, Wiley Interscience, New York, 1970, 1, pp. 413-512.
2. O. Mitsunobu, B. M. Trost, I. Fleming, Comprehensive Organic Synthesis Oxford, 1991, 6, p. 65.
3. R. S. Downing, P. J. Kunkeler, H. van Bekkum, Catal. Today 1997, 37, 121-136;
4. N. Ono, The Nitro Group in Organic Synthesis Wiley-VCH, Weinheim, 2001;
5. M. Suchy, P. Winternitz, M. Zeller, World Patent (WO) 91/00278, 1991.
6. F. Balkenhohl, C. V. D. Busche-Hunnefeld, A. Lansky, C. Zechel, Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2297;
7. Angew. Chem. 1996, 108, 2436-2488.
8. R. Kawahara, K.-I. Fujita, R. Yamaguchi, Adv. Synth. Catal. 2011, 353, 1161-1168;
9. W. X. Zhang, X. C. Dong, W. L. Zhao, Org. Lett. 2011, 13, 5386-5389;
10. K. Shimizu, M. Nishimura, A. Satsuma, ChemCatChem 2009, 1, 497-503;
11. K. Yamaguchi, J. L. He, T. Oishi, N. Mizuno, Chem. Eur. J. 2010, 16, 7199-7207;
12. P. R. Likhar, R. Arundhathi, M. L. Kantam, P. S. Prathima, Eur. J. Org. Chem. 2009, 5383-5389;
13. J. W. Kim, K. Yamaguchi, N. Mizuno, J. Catal. 2009, 263, 205-208.
14. A. W. Hofmann, Phil. Trans. R. Soc. Lond. 1850, 140, 93;
15. G. Solomons, C. Fryhle, Organic Chemistry, 7th Ed., Wiley, New York, 2000, p. 957;
16. R. B. C. Pillai, C. N. Pillai, Indian J. Chem. Sect. A 1990, 29, 1115.
17. H. Greenfield, Ind. Eng. Chem. Prod. Res. Dev. 1976, 15, 156-158;
18. M. Islam, P. Mondal, A. S. Roy, K. Tuhina, J. Mater. Sci. 2010, 45, 2484-2493.
19. M. Freifelder, Catalytic Hydrogenation in Organic Synthesis: Procedures and Commentary, Wiley, New York, 1978 (Chapt. 10);
20. R. E. Malz, H. Greenfield, Stud. Surf. Sci. Catal. 1991, 59, 351.
21. S. Das, S. Zhou, D. Addis, S. Enthaler, K. Junge, M. Beller, Top. Catal. 2010, 53, 979-984;
22. M. Stein, B. Breit, Angew. Chem. Int. Ed. 2013, 52, 2231-2234;
23. Angew. Chem. 2013, 125, 2287-2290.
24. P. Conti, D. Dermont, J. Cals, C. J. Ottenheijm, D. Leysen, Tetrahedron Lett. 1997, 38, 2915-2918.
25. L. Li, Z. Niu, S. Cai, Y. Zhi, H. Li, H. Rong, L. Liu, L. Liu, W. He, Y. Li, Chem. Commun. 2013, 49, 6843-6845;
26. C.-H. Tang, L. He, Y.-M. Liu, Y. Cao, H.-Y. He, K.-N. Fan, Chem. Eur. J. 2011, 17, 7172-7177;
27. M. Tajbakhsh, R. Hosseinzadeh, H. Alinezhad, S. Ghahari, A. Heydari, S. Khaksar, Synthesis 2011, 490-496;
28. B. Sreedhar, P. S. Reddy, D. K. Devi, J. Org. Chem. 2009, 74, 8806-8809;
29. F. Alonso, P. Riente, M. Yus, Synlett 2008, 1289-1292;
30. A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849-3862.
31. K. Weissermel, H. J. Arpe, Industrial Organic Chemistry, Wiley-VCH, Weinheim, 2003, pp. 376-378.
32. S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001, pp. 170-290.
33. F. Haber, Z Electrochem. 1898, 4, 410.
34. M. Freifelder, Handbook of Practical Catalytic Hydrogenation, Wiley, New York, 1971.
35. G. Wienhöfer, I. Sorribes, A. Boddien, F. Westerhaus, K. Junge, H. Junge, R. Liusar, M. Beller, J. Am. Chem. Soc. 2011, 133, 12875-12879.
36. C. Torres, C. Campos, J. G. Fierro, M. Oportus, P. Reyes, Catal. Lett. 2013, 143, 763-771;
37. F. Cárdenas-Lizana, S. Gomez-Quero, M. A. Keane, ChemSusChem 2008, 1, 215-221;
38. A. Corma, P. Serna, Science 2006, 313, 332-334.
39. U. Siegrist, P. Baumeister, H. U. Blaser, in Catalysis of Organic Reactions, Chemical Industries Series 75 (Eds.: F. Herkes, M. Dekker), CRC Press, 1998, pp. 207-219.
40. C.-H. Li, Z.-X. Yu, J. Mol. Catal. Chem. 2005, 226, 101-105;
41. M. Takasaki, Y. Motoyama, K. Higashi, S.-H.-Yoon, I. Mochida, H. Nagashima, Org. Lett. 2008, 10, 1601-1604.
42. H. U. Blaser, U. Siegrist, H. Steiner, M. Studer, in Aromatic Nitro Compounds: Fine Chemicals through Heterogeneous Catalysis (Eds.: R. A. Sheldon, H. van Bekkum), Wiley-VCH, Weinheim, 2001, p. 389.
43. L. P. Kuhn, J. Am. Chem. Soc. 1951, 73, 1510-1512.
44. C. F. H. Allen, J. van Allan, Org. Synth. Coll. 1955, 63;
45. P. Baumeister, H. U. Blaser, W. Scherrer, Stud. Surf. Sci. Catal. 1991, 59, 312.
46. J. Xiong, J. Chen, J. Zhang, Catal. Commun. 2007, 8, 345-350.
47. P. N. Rylander, Hydrogenation Methods, Academic Press, New York, 1985, p. 82-93.
48. H. Greenfield, F. S. Dovell, J. Org. Chem. 1967, 32, 3670-3671.
49. R. Braden, H. Knupfer, S. Hartung, US Patents 4, 002, 673 and 4, 051, 177, 1977.
50. A. J. Bechamp, Ann. Chim. Phys. 1854, 42, 186-196;
51. A. R. Cartolano, G. A. Vedage, Amines by Reduction, in Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley and Sons, New York, 2004, pp. 476-498;
52. A. Burawoy, J. P. Critchley, Tetrahedron 1959, 5, 340-351;
53. D. C. Gowda, B. Mahesh, S. Gowda, Indian J. Chem. Sect. B 2001, 40, 75-77.
54. J. H. Zagal, F. Bedioui, J.-P. Dodelet, N4-Macrocyclic Metal Complexes, Springer Science + Business Media, Inc., New York, 2006, pp. 83-126;
55. A. Bencini, V. Lippolis, Coord. Chem. Rev. 2010, 254, 2096-2180.
56. R. V. Jagadeesh, A.-E. Surkus, H. Junge, M.-M. Pohl, J. Radnik, J. Rabeah, H. Huan, V. Schünemann, A. Bruckner, M. Beller, Science 2013, 342, 1073-1076.
57. A. Corma, H. Garcia, F. X. Llabrési Xamena, Chem. Rev. 2010, 110, 4606-4655.
58. FA. Westerhaus, R. V. Jagadeesh, G. Wienhöfer, M.-M. Pohl, J. Radnik, A.-E. Surkus, J. Rabeah, K. Junge, H. Junge, M. Nielsen, A. Brückner, M. Beller, Nat. Chem. 2013, 5, 537-543.
59. E. J. Schwoegler, H. Adkins, J. Am. Chem. Soc. 1939, 61, 3499-3502.
60. O. Saidi, A. J. Blacker, M. M. Farah, S. P. Marsden, J. M. Williams, Angew. Chem. Int. Ed. 2009, 48, 7375-7378;
61. Angew. Chem. 2009, 121, 7511-7514;
62. F. Qi, L. Hu, S. Lu, X. Cao, H. Gu, Chem. Commun. 2012, 48, 9631-9633.
63. R. F. Borch, A. I. Hassid, J. Org. Chem. 1972, 37, 1673-1674;
64. J. Zhang, P. G. Blazecka, J. G. Davidson, Org. Lett. 2003, 5, 553-556.
65. F. Santoro, R. Psaro, N. Ravasio, F. Zaccheria, ChemCatChem 2012, 4, 1249-1254.
66. J. Volf, J. Pasek, Stud. Surf. Sci. Catal. (Catalytic Hydrogenation, Ed.: L. Cerveny), Elsevier, Amsterdam, 1986, 27, pp. 105-144.
67. S. Sato, T. Sakamoto, E. Miyazawa, Y. Kikugawa, Tetrahedron 2004, 60, 7899-7906.
68. R. W. Layer, Chem. Rev. 1963, 63, 489-510.