Gold-catalyzed heterogeneous aerobic dehydrogenative amination of α,β-unsaturated aldehydes to enaminals

Angewandte Chemie - International Edition

Volumn 53, Issue 2, 2014, Pages 455-458

  Jin, Xiongjie ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

aldehydes; amines; dehydrogenative amination; gold; heterogeneous catalysis

Indexed keywords

ENAMINONES; GOLD NANOPARTICLES; HETEROGENEOUS CATALYST; HIGH YIELD; OCTAHEDRAL MOLECULAR SIEVES; SYNTHETIC PROCEDURES; UNSATURATED ALDEHYDES; WACKER-TYPE OXIDATION;

ALDEHYDES; CATALYSIS; GOLD; MANGANESE; MANGANESE OXIDE; METAL NANOPARTICLES; MOLECULAR SIEVES;

AMINES;

EID: 84891751071     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308260     Document Type: Article

References (59)

1. S. G. Zlotin, P. G. Kislitsin, A. V. Samet, E. A. Serebryakov, L. D. Konyushkin, V. V. Semenov, J. Org. Chem. 2000, 65, 8430
2. H. Liu, X. Liang, H. Søhoel, A. Bülow, M. Bols, J. Am. Chem. Soc. 2001, 123, 5116
3. N. Nishiwaki, T. Ogihara, T. Takami, M. Tamura, M. Ariga, J. Org. Chem. 2004, 69, 8382
4. H. Kuwabara, K. Umihara, Y. Furugori, I. Itoh, Chem. Lett. 2005, 34, 834
5. L. E. Kiss, H. S. Ferreira, D. A. Learmonth, Org. Lett. 2008, 10, 1835
6. Q. Sun, R. Wu, S. Cai, Y. Lin, L. Sellers, K. Sakamoto, B. He, B. R. Peterson, J. Med. Chem. 2011, 54, 1126
7. M.-E. Theoclitou, B. Aquila, M. H. Block, P. J. Brassil, L. Castriotta, E. Code, M. P. Collins, A. M. Davies, T. Deegan, J. Ezhuthachan, S. Filla, E. Freed, H. Hu, D. Huszar, M. Jayaraman, D. Lawson, P. M. Lewis, M. V. P. Nadella, V. Oza, M. Padmanilayam, T. Pontz, L. Ronco, D. Russell, D. Whitston, X. Zheng, J. Med. Chem. 2011, 54, 6734
8. S. Muthusaravanan, B. D. Bala, S. Perumal, Tetrahedron Lett. 2013, 54, 5302
9. T. R. Swaroop, H. Ila, K. S. Rangappa, Tetrahedron Lett. 2013, 54, 5288.
10. B. Stanovnik, J. Svete, Chem. Rev. 2004, 104, 2433, and Refs therein
11. A. Z. A. Elassar, A. A. El-Khair, Tetrahedron 2003, 59, 8463
12. J. V. Greenhill, Chem. Soc. Rev. 1977, 6, 277.
13. J. Dabrowski, K. Kamienska-Trela, J. Am. Chem. Soc. 1976, 98, 2826
14. M. d'Ischia, A. Napolitano, C. Costantini, Tetrahedron 1995, 51, 9501
15. S. K. Chatterjee, W.-D. Rudorf, Phosphorus Sulfur Silicon Relat. Elem. 1998, 133, 251
16. J. Clayden, N. Greeves, S. Warren, Organic Chemistry, Oxford University Press, New York, 2012
17. Z.-P. Lin, F. F. Wong, Y.-B. Chen, C.-H. Lin, M.-T. Hsieh, J.-C. Lien, Y.-H. Chou, H.-C. Lin, Tetrahedron 2013, 69, 3991.
18. S. S. Stahl, Angew. Chem. 2004, 116, 3480
19. Angew. Chem. Int. Ed. 2004, 43, 3400
20. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
21. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981, and Refs therein.
22. J. J. Bozell, L. S. Hegedus, J. Org. Chem. 1981, 46, 2561
23. L. S. Hegedus, B. Akermark, K. Zetterberg, L. F. Olsson, J. Am. Chem. Soc. 1984, 106, 7122
24. M. Beller, M. Eichberger, H. Trauthwein, Angew. Chem. 1997, 109, 2306
25. Angew. Chem. Int. Ed. Engl. 1997, 36, 2225
26. M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Muller, Eur. J. Inorg. Chem. 1999, 1121
27. Y. Obora, Y. Shimizu, Y. Ishii, Org. Lett. 2009, 11, 5058
28. Y. Shimizu, Y. Obora, Y. Ishii, Org. Lett. 2010, 12, 1372
29. L. L. Chng, J. Zhang, J. Yang, M. Amoura, J. Y. Ying, Adv. Synth. Catal. 2011, 353, 2988
30. Y. Mizuta, K. Yasuda, Y. Obora, J. Org. Chem. 2013, 78, 6332
31. Y. Yang, F. Ni, W.-M. Shu, S.-B. Yu, M. Gao, A.-X. Wu, J. Org. Chem. 2013, 78, 5418
32. X. Ji, H. Huang, W. Wu, H. Jiang, J. Am. Chem. Soc. 2013, 135, 5286.
33. S. Ueno, R. Shimizu, R. Kuwano, Angew. Chem. 2009, 121, 4613
34. Angew. Chem. Int. Ed. 2009, 48, 4543.
35. [5e,f] under the conditions described in TableS1 (dimethylformamide was used as a solvent instead of THF), the desired product 3 aa was not obtained. In this case, 1 a was mostly decomposed to benzaldehyde (retro-aldol reaction; 18 % yield) and other unidentified byproducts; see:, D. Enders, T. V. Nguyen, Tetrahedron Lett. 2012, 53, 2091.
36. Y.-C. Son, V. D. Makwana, A. R. Howell, S. L. Suib, Angew. Chem. 2001, 113, 4410
37. Angew. Chem. Int. Ed. 2001, 40, 4280
38. T. Oishi, K. Yamaguchi, N. Mizuno, ACS Catal. 2011, 1, 1351
39. K. Yamaguchi, H. Kobayashi, T. Oishi, N. Mizuno, Angew. Chem. 2012, 124, 559
40. Angew. Chem. Int. Ed. 2012, 51, 544
41. K. Yamaguchi, Y. Wang, T. Oishi, Y. Kuroda, N. Mizuno, Angew. Chem. 2013, 125, 5737
42. Angew. Chem. Int. Ed. 2013, 52, 5627.
43. J. Mielby, S. Kegnæs, P. Fristrup, ChemCatChem 2012, 4, 1037.
44. Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. 2011, 123, 9079
45. Angew. Chem. Int. Ed. 2011, 50, 8917
46. J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 18550
47. J. Zhu, Y. Zhang, F. Shi, Y. Deng, Tetrahedron Lett. 2012, 53, 3178.
48. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
49. Kaneda and co-workers have recently reported that electron-deficient internal alkenes could be oxidized to the corresponding ketones by a palladium-catalyzed formal Wacker-type oxidation using molecular oxygen as the sole oxidant; α,β-unsaturated aldehydes were not used as substrates; see:, T. Mitsudome, S. Yoshida, T. Mizugaki, K. Jitsukawa, K. Kaneda, Angew. Chem. 2013, 125, 6077
50. Angew. Chem. Int. Ed. 2013, 52, 5961.
51. T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566
52. Y. Izawa, D. Pun, S. S. Stahl, Science 2011, 333, 209
53. T. Diao, T. J. Wadzinski, S. S. Stahl, Chem. Sci. 2012, 3, 887
54. W. Gao, Z. He, Y. Qian, J. Zhao, Y. Huang, Chem. Sci. 2012, 3, 883
55. A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851
56. Y. Izawa, C. Zheng, S. S. Stahl, Angew. Chem. 2013, 125, 3760
57. Angew. Chem. Int. Ed. 2013, 52, 3672
58. T. Diao, D. Pun, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 8205
59. D. Pun, T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 8213.