Efficient and selective room-temperature gold-catalyzed reduction of nitro compounds with CO and H2O as the hydrogen source

Angewandte Chemie - International Edition

Volumn 48, Issue 50, 2009, Pages 9538-9541

  He, Lin ^a   Wang, Lu Cun ^a   Sun, Hao ^a   Ni, Ji ^a   Cao, Yong ^a   He, Yong ^a   Fan, Kang Nian ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Chemoselectivity goldnitro compounds; Reduction; Sustainable chemistry

Indexed keywords

CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; CHEMOSELECTIVITY-GOLDNITRO COMPOUNDS; ENVIRONMENTALLY-FRIENDLY; GOLD CATALYSIS; HIGH YIELD; HYDROGEN SOURCES; REDUCTANTS; REDUCTION OF NITRO COMPOUNDS; ROOM TEMPERATURE; SELECTIVE REDUCTION; SUSTAINABLE CHEMISTRY;

CHEMICAL REACTIONS; FUNCTIONAL GROUPS;

CHEMICAL COMPOUNDS;

EID: 73249151525     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904647     Document Type: Article

References (52)

1. a) P. N. Rylander, Hydrogenation Methods, Academic Press, London, 1985, pp. 104-117;
2. b) S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, Chichester, 2001, pp. 315-387;
3. c) J.P. Adams, J. R. Paterson, J. Chem. Soc. Perkin Trans 1 2000, 3695-3705.
4. a) J. G. Lee, K. I. Choi, H. Y. Koh, Y. Kim, Y. Kang, Y. S. Cho, Synthesis 2001, 81-84;
5. b) Y. Liu, Y. Lu, M. Prashad, O. Repič, T.J. Blacklock, Adv. Synth. Catal. 2005, 347, 217-219;
6. c) S. Chandrasekhar, S. J. Prakash, C. L. Rao, J. Org. Chem. 2006, 71, 2196-2199;
7. d) S. Iyer, G. M. Kulkami, Synth. Commun. 2004, 34, 111 -725;
8. e) A. Corma, P. Serna, P. Concepción, J. C. José, J. Am. Chem. Soc. 2008, 750, 8748-8753;
9. f) D. He, H. Shi, Y. Wu, B. Q. Xu, Green Chem. 2007, 9, 849-851.
10. a) M. L. Kantam, R. Chakravarti, U. Pal, B. Sreedhar, S. Bhargava, Adv. Synth. Catal. 2008, 350, 822-827;
11. b) J. L. Zhang, Y. Wang, H. Ji, Y. G. Wei, N. Z. Wu, B. J. Zuo, Q. Wang, J. Catal. 2005, 229, 114-118.
12. a) S. Cenini, F. Ragaini, Catalytic Reductive Carbonytation of Organic Nitro Compounds, Kluwer, Dordrecht, 1996, pp. 132-160;
13. b) A. M. Tafesh, J. Weiguny, Chem. Rev. 1996, 96, 2035-2052;
14. c) K. Nomura, J. Mol. Catal. A 1998, 130, 1-28.
15. a) F. Ragaini, S. Cenini, J. Mol. Catal. A 1996, 105, 145-148;
16. b) K. Nomura, M. Ishino, M. Hazama, Bull. Chem. Soc. Jpn. 1991, 64, 2624-2628;
17. c) A. J. Pardey, M. Fernandez, A. B. Rivas, M. C. Ortega, C. Urbina, D. Moronta, C. Longo, M. Mediavilla, P. J. Baricelli, S. A. Moya, Inorg. Chim. Acta 2002, 329, 22-30;
18. d) S. Moya, R. Sariego, P. Aguirre, R. Sartori, P. Dixneuf, Bull. Soc. Chim. Belg. 1995, 104, 19-25;
19. e) J. Y. Jiang, J. T. Mei, Y. H. Wang, F. Wen, Z. L. Jin, AppL Catal. A 2002, 224, 21-25.
20. a) L. Q. Liu, B. T. Qiao, Z. J. Chen, J. Zhang, Y. Q. Deng, Chem. Commun. 2009, 653 - 655;
21. b) X. Z. Liu, S. W. Lu, J. Mol. Catal. A 2004, 272, 127-130;
22. c) F. Ragaini, S. Cenini, M. Gasperini, J. Mol. Catal. A 2001, 174, 51-57;
23. d) K. Nomura, J. Mol. Catal. A 1995, 95, 203-210.
24. a) G. J. Rodriguez-Rivera, W. B. Kim, S. T. Evans, T. Voitl, J. A. Dumesic, J. Am. Chem. Soc. 2005, 127, 10790-10791;
25. b) H. Tsunoyama, H. Sakurai, Y. Negishi, T. Tsukuda, J. Am. Chem. Soc. 2005, 127, 9374-9375;
26. c) M. Haruta, Nature 2005, 437, 1098-1099;
27. d) A. Corma, P. Sema, Science 2006, 313, 332-334;
28. e) M. Haruta, Catal. Today 1997, 36, 153-166;
29. f) X. Zhang, H. Shi, B. Q. Xu, Angew. Chem. 2005, 117, 7294-7297;
30. Angew. Chem. Int Ed. 2005, 44, 7132-7135.
31. a) C. Delia Pina, E. Falletta, L. Prati, M. Rossi, Chem. Soc. Rev. 2008, 37, 2077-2095;
32. b) F. Z. Su, Y. M. Liu, L. C. Wang, Y. Cao, H. Y. He, K. N. Fan, Angew. Chem. 2008, 120, 340-343;
33. Angew. Chem. Int. Ed. 2008, 47, 334-337;
34. c) T. A. Nijhuis, T. Visser, B. M. Weckhuysen, J. Phys Chem. B 2005, 109, 19309-19319;
35. d) N. Yap, R. P. Andres, W. N. Delgass, J. Catal. 2004, 226, 156-170.
36. a) C. Mohr, H. Hofmeister, J. Radnik, P. Claus, J. Am. Chem. Soc. 2003, 125, 1905-1911;
37. b) G. C. Bond, P. A. Sermon, Gold Bull. 1973, 6, 102-105.
38. A. Corma, P. Serna, H. Garcia, J. Am. Chem. Soc. 2007, 129, 6358-6359.
39. a) C. Milone, M. L. Tropeano, P. Gulino, R. Ingaglia, G. Neri, S. Galvagno, Chem. Commun. 2002, 868-869;
40. b) P. Sema, P. Concepción, A. Corma, J. Catal. 2009, 265, 19-25.
41. a) G. C. Bond, D. T. Thompson, Gold Bull. 2000, 33, 41-45;
42. b) B. K. Min, C. M. Friend, Chem. Rev. 2007, 107, 2709-2724.
43. ∞ variation in the range of the study (1-5 atm) reveals that CO activation occurs through the preequilibrium formation of a surface-adsorbed carbonyl species.
44. The reduction did not proceed when other unsaturated compounds without a nitro group (styrene, acetophenone, benzalde hyde, and benzonitrile) were tested as substrates under the same conditions (see Table S2 in the Supporting Information).
45. A. Karpenko, R. Leppelt, V. Plzak, J. Cai, A. Chuvilin, B. Schumacher, U. Kaiser, R. J. Behm, Top. Catal. 2007, 44, 183-198.
46. a) M. Conte, H. Miyamura, S. Kobayashi, V. Chechik, J. Am. Chem. Soc. 2009, 131, 7189-7196;
47. b) A. Abad, C. Almela, A. Corma, H. Garcia, Chem. Commun. 2006, 3178-3180.
48. a) C. Lemire, R. Meyer, Sh. K. Shaikhutdinov, H.-J. Freund, Surf. Sci. 2004, 552, 27-34;
49. b) C. Lemire, R. Meyer, Sh. Shaikhutdinov, H.-J. Freund, Angew. Chem. 2004, 116, 121-124;
50. Angew. Chem. Int. Ed. 2004, 43, 118-121;
51. c) A. Sandoval, A. Gómez-Cortés, R. Zanella, G. Diaz, J. M. Saniger, J. Mol. Catal. A 2007, 278, 200-208;
52. d) J. A. Rodriguez, J. Evans, J. Graciani, J. B. Park, P. Liu, J. Hrbek, J. F. Sanz, J. Phys. Chem. C 2009, 113, 7364-7370.