Heterogeneously catalyzed aerobic oxidative biaryl coupling of 2-naphthols and substituted phenols in water

Journal of the American Chemical Society

Volumn 127, Issue 18, 2005, Pages 6632-6640

  Matsushita, Mitsunori ^a   Kamata, Keigo ^b   Yamaguchi, Kazuya ^a,b   Mizuno, Noritaka ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OXIDATION; REACTION KINETICS; RUTHENIUM; SUBSTITUTION REACTIONS;

2-NAPHTHOLS; BIARYL COMPOUNDS; OXIDANTS; REOXIDATION;

PHENOLS;

1,2 DICHLOROETHANE; 2 NAPHTHOL; ACETONITRILE; ETHYLENE GLYCOL DIMETHYL ETHER; OXIDIZING AGENT; OXYGEN; PHENOL DERIVATIVE; RUTHENIUM DERIVATIVE; RUTHENIUM HYDROXIDE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; ELECTRON SPIN RESONANCE; OXIDATION; OXIDATIVE COUPLING; SUBSTITUTION REACTION;

EID: 18644368601     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050436k     Document Type: Article

References (80)

1. (a) Taylor, W. I.; Buttersby, A. R. Oxidative Coupling of Phenols; Marcel Dekker: New York, 1967.
2. (b) Bringmann, G.; Walter, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
3. (c) Nasir, M. S.; Cohen, B. I.; Karlin, K. D. J. Am. Chem. Soc. 1992, 114, 2482.
4. (d) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563.
5. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
6. (b) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
7. (c) Noyori, R. Tetrahedron 1994, 50, 4259.
8. (d) Trost, B. M. Pure Appl. Chem. 1992, 64, 315.
9. (e) Hayashi, T.; Kudo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421.
10. (f) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
11. (g) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
12. (h) Blaser, H.-U. Chem. Rev. 1992, 92, 935.
13. (i) Rosini, G.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
14. (j) Pu, L. Chem. Rev. 1998, 98, 2405.
15. (k) Kočovský, P.; Vyskočil, S.; Smŕcina, M. Chem. Rev. 2003, 103, 3213.
16. (l) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
17. (a) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007.
18. (b) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134.
19. (c) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y. Tetrahedron 1996, 52, 1005.
20. (d) Hovorka, M.; Günterová, J.; Závada, I. Tetrahedron Lett. 1990, 31, 413.
21. (e) Doussot, J.; Guy, A.; Ferroud, C. Tetrahedron Lett. 2000, 41, 2545.
22. (f) Nishino, H.; Itoh, N.; Nagashima, M.; Kurosawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 620.
23. Examples of catalytic aerobic oxidative biaryl coupling (homogeneous system): (a) Sharma, V. B.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44, 2655.
24. (b) Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
25. (c) Hwang, D.-R.; Chen, C.-P.; Uang, B.-J. Chem. Commun. 1999, 1207.
26. (d) Yadav, J. S.; Reddy, B. V. S.; Gayathri, K. U.; Prasad, A. R. New J. Chem. 2003, 27, 1684.
27. (e) Umare, P. S.; Tembe, G. L. React. Kinet. Catal. Lett. 2004, 82, 173.
28. (f) Gupta, R.; Mukherjee, R. Tetrahedron Lett. 2000, 41, 7763.
29. (g) Nishino, H.; Satoh, H.; Yamashita, M.; Kurosawa, K. J. Chem. Soc., Perkin Trans. 2 1999, 1919.
30. (h) Umare, P. S.; Tembe, G. L. React. Kinet. Catal. Lett. 2004, 82, 173.
31. Examples of catalytic aerobic oxidative biaryl coupling (heterogeneous system): (a) Prasad, M. R.; Kamalakar, G.; Kulkarni, S. J.; Raghavan, K. V. J. Mol. Catal. A 2002, 180, 109.
32. (b) Armengol, E.; Corma, A.; García, H.; Primo, J. Eur. J. Org. Chem. 1999, 1915, 5.
33. (c) Kantam, M. L.; Kavita, B.; Figueras, F. Catal. Lett. 1998, 51, 113.
34. (d) Mastrorilli, P.; Muscio, F.; Suranna, G. P.; Nobile, C. F.; Latronico, M. J. Mol. Catal. A 2001, 165, 81.
35. (e) Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1997, 62, 3194.
36. (f) Iwai, K.; Yamauchi, T.; Hashimoto, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Lett. 2003, 32, 58.
37. (g) Fujiyama, H.; Kohara, I.; Iwai, K.; Nishiyama, S.; Tsuruya, S.; Masai, M. J. Catal. 1999, 188, 417.
38. Examples of enantioselective biaryl coupling: (a) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
39. (b) Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137.
40. (c) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980.
41. (d) Somei, H.; Asano, Y.; Yoshida, T.; Takizawa, S.; Yamataka, H.; Sasai, H. Tetrahedron Lett. 2004, 45, 1841.
42. (e) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Angew. Chem., Int. Ed. 2002, 41, 4532.
43. (f) Gao, J.; Reibenspies, J. H.; Martell, A. E. Angew. Chem., Int. Ed. 2003, 42, 6008.
44. (g) Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000, 1433.
45. (h) Li, X.; Hewglay, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
46. (i) Tada, M.; Taniike, T.; Kantam, L. M.; Iwasawa, Y. Chem. Commun. 2004, 2542.
47. (j) Barhatre, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529.
48. Sheldon, R. A.; van Bekkum, H. Fine Chemical through Heterogeneous Catalysis; Wiley: Weinheim, 2001.
49. (a) Li, C.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
50. (b) Grieco, P. A. Organic Synthesis in Water, Blacky Academic Professional: London, 1998.
51. (c) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: London, 1998.
52. (d) Sheldon, R. A. Green Chem. 2000, 2, G1.
53. (e) Anastas, P. T.; Bartlett, L. B.; Kirchhoff, M. M.; Williamson, T. C. Catal. Today 2000, 55, 11.
54. (f) Thematic issue on "Organic Reaction in Water". Adv. Synth. Catal. 2002, 3-4, 219-451 and references therein.
55. Cotton, F. A.; Wilkinson, G.; Gauss, P. L. Basic Inorganic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1995.
56. 3, 41% yield of 1b was obtained at 88% conversion of 1a under the same reaction conditions.
57. Sheldon, R. A.; Wallau, M.; Arends, I. W. C. E.; Schuchardt, U. Acc. Chem. Res. 1998, 31, 485.
58. (a) Schouten, A. J.; Challa, G.; Eeedijk, J. J. Mol. Catal. 1980, 9, 41.
59. (b) Pandey, G.; Muralikrishna, C.; Bhalerao, U. T. Tetrahedron Lett. 1990, 31, 3771.
60. (a) Smŕcina, M.; Vyskǒcil, S.; Máca, B.; Poláxf0ek, M.; Claxton, T. A.; Abbott, A. P.; Kǒcovsk'y, P. J. Org. Chem. 1994, 59, 2156.
61. (b) Hovorka, M.; Šcigel, R.; Gunterová, J.; Tichxc, M.; Závada, J. Tetrahedron 1992, 48, 9503.
62. (c) Hovorka, M.; Závada, J. Tetrahedron 1992, 48, 9517.
63. The data were taken from ref 13a.
64. (a) Yamaguchi, K.; Matsushita, M.; Mizuno, N. Angew. Chem., Int. Ed. 2004, 43, 1576.
65. (b) Kamata, K.; Kasai, J.; Yamaguchi, K.; Mizuno, N. Org. Lett. 2004, 6, 3577.
66. For the anion-radical coupling mechanism, more easily reducible 11a is reduced to form the anionic species, while the radical from 1a prefers to act as an electrophilic radical. Therefore, the radical from 1a preferably interacts with the anion from 11a rather than that from 1a, giving the cross-coupling products predominantly. See ref 13a.
67. Church, D. F. Anal. Chem. 1994, 66, 419.
68. (a) Mitchell, P. C. H.; Scott, C. E.; Bonnelle, J. P.; Grimblot, J, G. J. Catal. 1987, 107, 482.
69. (b) Nagai, M.; Koizumi, K.; Omi, S. Catal. Today 1997, 35, 393.
70. (c) Murata, S.; Aika, K. J. Catal. 1992, 136, 110.
71. (d) Aika, K.; Ohya, A.; Ozaki, A.; Inoue, Y.; Yasumori, I. J. Catal. 1985, 92, 305.
72. (e) Williams, G. P. In CRC Handbook of Chemistry and Physics, 82nd ed.; Lida, D. R., Ed.; CRC Press: Washington, DC, 2001; Section 10, pp 200-205.
73. -1).
74. (a) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538.
75. (b) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480.
76. (c) Yamaguchi, K.; Mizuno, N. Chem.-Eur. J. 2003, 9, 4353.
77. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
78. (a) Stevens, W.; Basch, H.; Krauss, J. J. Chem. Phys. 1984, 81, 6026.
79. (b) Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612.
80. (c) Cundari, T. R.; Stevens, W. J. J. Chem. Phys. 1993, 98, 5555.