Chemoselective synthesis of substituted imines, secondary amines, and β-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts

Chemistry - A European Journal

Volumn 15, Issue 33, 2009, Pages 8196-8203

  Santos, Laura L ^a   Serna, Pedro ^a   Corma, Avelino ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Cascade reactions chemoselectivity; Gold; Hydrogenation; Nitro compounds

Indexed keywords

AROMATIC AMINES; BI-FUNCTIONAL CATALYSTS; BIFUNCTIONAL; CARBONYL COMPOUNDS; CASCADE REACTIONS; CASCADE REACTIONS CHEMOSELECTIVITY; CHEMO-SELECTIVITY; CHEMOSELECTIVE; CHEMOSELECTIVE HYDROGENATION; CINNAMATES; DOUBLE BONDS; EX SITU; GOLD CATALYSTS; GOLD-CATALYZED REACTIONS; HYDROAMINATIONS; IN-SITU; IN-SITU FORMATIONS; MICHAEL ADDITIONS; MILD REACTION CONDITIONS; NITRO COMPOUNDS; NITRO GROUP; NITRO-AROMATICS; NITROAROMATIC COMPOUND; SECONDARY AMINES; SOLID CATALYSTS; SUBSTITUTED ANILINES; SYNTHETIC ROUTES; TANDEM REACTION; UNSATURATED CARBONYL COMPOUNDS; UNSATURATED IMINES;

ACETYLENE; ADDITION REACTIONS; ALDEHYDES; AMINATION; AMINES; ANILINE; AROMATIC COMPOUNDS; AROMATIC HYDROCARBONS; CARBONYLATION; CATALYSIS; CATALYSTS; CYANIDES; GOLD; HYDROGENATION; REACTION KINETICS; SILANES; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

COMPLEXATION;

EID: 68949144618     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900884     Document Type: Article

References (83)

1. A. Corma, P. Serna, Science 2006, 313, 332-334.
2. A. Grirrane, A. Corma, H. Garcia, Science 2008, 322, 1661-1664.
3. A. Corma, P. Conceptión, P. Serna, Angew. Chem. 2007, 119, 7404-7407;
4. Angew. Chem. Int. Ed. 2007, 46, 7266-7269.
5. A. Corma, P. Serna, Nat Protoc. 2007, 1, 2590-2595.
6. M. Boronat, P. Conceptión, A. Corma, S. González, F. Illas, P. Serna, J. Am. Chem. Soc. 2007, 129, 16230-16237.
7. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis Wiley-VCH, Weinheim, 2006, p. 672.
8. L. P. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
9. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
10. L. P. Tietze, Chem. Rev. 1996, 96, 115-136.
11. H. Pellissier, Tetrahedron 2006, 62, 1619-1665.
12. T.-L. Ho in Tandem Organic Reactions, Wiley, New York, 1992, p. 502.
13. R. A. Bunce, Tetrahedron 1995, 52, 13103-13159.
14. B. M. Trost, Science 1991, 254, 1471-1477.
15. B. M. Trost, Angew. Chem. 1995, 107, 285-307;
16. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
17. R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233-1246.
18. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069.
19. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151.
20. C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 3451-3453.
21. S. Vargas, M. Rubio, A. Suárez, A. Pizzano, Tetrahedron Lett. 2005, 46, 2049-2052.
22. L. Zani, C. Bolm, Chem. Commun. 2006, 4263-4275.
23. C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 9584-9585.
24. X. Zhang, A. Corma, Angew. Chem. 2008, 120, 4430-4433;
25. Angew. Chem. Int. Ed. 2008, 47, 4358-4361.
26. B. Jiang, Y.-G. Si, Tetrahedron Lett. 2003, 44, 6161-6169,.
27. R. Bloch, Chem. Rev. 1998, 98, 1407-1438.
28. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
29. S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 226, 8797-8798.
30. S. C. Pan, J. Zhou, B. List, Angew. Chem. 2007, 119, 618-620;
31. Angew. Chem. Int. Ed. 2007, 46, 612-614.
32. D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
33. A. Ajamian, G.J. L. Leason, Angew. Chem. 2004, 116, 3842-3848;
34. Angew. Chem. Int. Ed. 2004, 43, 3754-3760.
35. D. J. Hadjipavlou-Litina, A. A. Geronikaki, Drug Des. Discovery 1998, 25, 199-206.
36. M. Cushman, H. M. He, C. M. Lin, E. Hamel, J. Med. Chem. 1993, 36, 2817-2821.
37. Y.-L. Zhong, S. W. Krska, H. Zhou, R. A. Reamer, J. Lee, Y. Sun, D. Askin, Org. Lett. 2009, 11, 369-372.
38. E. M. Gordon, R.W. Barret, W.J. Dower, S. P. A. Fodor, M. A. Gallop, J. Med. Chem. 1994, 37, 1385-1401.
39. D. B. Sharp in Herbicides: Chemistry, Degradation, and Mode of Action (Eds.: P. C. Kearney, D. D. Kaufman), Marcel Dekker, New York, 1988, Chapter 7.
40. M. M. Sprung, Chem. Rev. 1940, 26, 297-338.
41. R. W. Layer, Chem. Rev. 1963, 63, 489-510.
42. K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem. 2003, 115, 4211-4216;
43. Angew. Chem. Int. Ed. 2003, 42, 4077-4082.
44. B. Zhu, M. Lazar, B. G. Trewyn, R. J. Angelici, J. Catal. 2008, 260, 1-6.
45. B. Zhu, R. J. Angelici, Chem. Commun. 2007, 2157-2159.
46. A. Korich, T. S. Hughes, Synlett 2007, 2602-2604.
47. M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122;
48. Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
49. M. Misra, R. Luthra, K. L. Singh, K. Sushil in Comprehensive Natural Products Chemistry, Vol. 4 (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Pergamon, Oxford, 1999, p. 25.
50. J. Staunton, B. Wilkinson, Top. Curr. Chem. 1998, 195, 49-92.
51. C.B. Pollard, G. C. Mattson, J. Am. Chem. Soc. 1956, 78, 4089-4090.
52. Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley-VCH, New York, 1997.
53. G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117-128.
54. J. Kant, D. G. Walker in The Organic Chemistry of beta-Lactams (Ed.: G. I. Georg), VCH Publishers, New York, 1993.
55. E. R Kleinman in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Pleming), Pergamon Press, Oxford, 1991, p. 893.
56. S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
57. P. N Devine, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron 1997, 53, 6739-6746.
58. Y F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 1982, 204, 6465-6466.
59. Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
60. K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524.
61. E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475.
62. H. Fujieda, M. Kanai, T. Kambara, A. lida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061.
63. N. Halland, P. S. Aburel, K. A. Jorgensen, Angew. Chem. 2004, 116, 1292-1297;
64. Angew. Chem. Int. Ed. 2004, 43, 1272-1277.
65. A. E. Wroblewski, V. Bansal, P. Kisanga, J. G. Verkade, Tetrahedron 2003, 59, 561-566.
66. M. Sani, L. Bruche, G. Chiva, S. Fustero, J. Piera, A. Volonterio, M. Zanda, Angew. Chem. 2003, 115, 2106-2109;
67. Angew. Chem. Int. Ed. 2003, 42, 2060-2063.
68. P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis, Pergamon, New York, 1992, p. 114.
69. N. B. Ambhaikar, J. P. Snyger, D. C. Liotta, J. Am. Chem. Soc. 2003, 125, 3690-3691.
70. L. Fadini, A. Togni, Chem. Commun. 2003, 30-31.
71. J. C. Adrian, M. L. Snapper, J. Org. Chem. 2003, 68, 2143-2150.
72. G. Bartoli, M. Bosco, E. Marcantoni, M. Petrini, L. Sambri, E. Torregiani, J. Org. Chem. 2001, 66, 9052-9055.
73. T. P. Loh, L. L. Wei, Synlett 1998, 975-976.
74. D. Enders, S. F. Muller, G. Raabe, J. Runsink, Eur. J. Org. Chem. 2000, 879-892.
75. R. Varala, M. M. Alam, S. R. Adapa, Synlett 2003, 720-722.
76. T. C. Wabnitz, J. B. Spencer, Tetrahedron Lett. 2002, 43, 3891-3894.
77. N. Azizi, M. R. Saidi, Tetrahedron 2004, 60, 383-387.
78. M. L. Kantam, V. Neeraja, B. Kavita, B. Neelima, M. K. Chaudhuri, S. Hussain, Adv. Synth. Catal. 2005, 347, 763-766.
79. J.-M. Xu, Q. Wu, Q.-Y Zhang, F. Zhang, X.-F. Lin, Eur. J. Org. Chem. 2007, 1798-1802.
80. K. Kristan, Š. Starčević, M. Brunskole, T. L. Rižner, S. Gobec, Mol. Cell. Endocrinol. 2006, 248, 239-241.
81. S. Toshiya, H. Hamako (Takasago Perfumery Co LTD), US Patent 5180586, 1993.
82. D. Dennis, B. Noel (Standard Oil Co.), US Patent 4507212, 1985.
83. A. Corma, P. Conceptión, I. Domínguez, V. Fornés, M. J. Sabater, J. Catal. 2007, 252, 39-47.