Hydrogenation of arenes under mild conditions using rhodium pyridylphosphine and bipyridyl complexes tethered to a silica-supported palladium heterogeneous catalyst

Organometallics

Volumn 19, Issue 4, 2000, Pages 622-629

  Yang, Hong ^a   Gao, Hanrong ^a   Angelici, Robert J ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000226859     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990713u     Document Type: Article

References (88)

1. (a) Brunner, H. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W. A., Eds.; VCH: Weinheim, Germany, 1996; pp 201-219.
2. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 523-549.
3. (c) James, B. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, pp 285-369.
4. (d) James, B. R. Homogeneous Hydrogenation; Wiley: New York, 1973.
5. (e) Dickson, R. S. Homogeneous Catalysis with Compounds of Rhodium and Iridium; Reidel: Dordrecht, The Netherlands, 1985.
6. (a) Halpern, J. Science 1982, 217, 401.
7. (b) Hosteller, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1990, 112, 8621.
8. (c) Schwartz, J., Labinger J A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
9. (d) Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 4450.
10. (e) Crabtree, R. H. Acc. Chem. Res. 1990, 23, 95.
11. (f) Traker, J. R.; Riley, D. P. J. Organomet. Chem. 1985, 279, 49.
12. (g) Mirbach, M. J.; Tuyet, N. P.; Saus, A. J. Organomet. Chem. 1982, 236, 309.
13. (h) Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681.
14. (a) Brunner, H.; Zettlmeier, W. In Advances in Catalytic Processes; Doyle, M. P., Ed.; Jay Press: Greenwich, CT, 1995; p 1.
15. (b) Trost, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
16. (a) Yu, J. S.; Ankianiec, B. C.; Nguyen, M. T.; Rothwell, I. P. J. Am. Chem. Soc. 1992, 114, 1927.
17. (b) Profilet, R. D.; Rothwell, A. P.; Rothwell, I. P. J. Chem. Soc., Chem. Commun. 1993, 42.
18. (c) Ankianiec, B. C.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1991, 113, 4710.
19. (d) Steffey, B. D.; Rothwell, I. P. J. Chem. Soc., Chem. Commun. 1990, 213.
20. (e) Steffey, B. D.; Chesnut, R. W.; Kerschner, J. L.; Pellechia, P. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1989, 111, 378.
21. (a) Muetterties, E. L.; Bleeke, J. R. Acc. Chem. Res. 1979, 12, 324.
22. (b) Bleeke, J. R.; Muetterties, E. L. J. Am. Chem. Soc. 1981, 103, 556.
23. (c) Wilczynski, R.; Fordyce, W. A.; Halpern, J. J. Am. Chem. Soc. 1983, 105, 2066.
24. (d) Linn, D. E., Jr.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 2969.
25. (e) Stobart, S. R.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1984, 1700.
26. (f) Rothwell, I. P. J. Chem. Soc., Chem. Commun. 1997, 1331.
27. (a) Amer, I.; Amer, H.; Blum, J. J. Mol. Catal. 1986, 34, 221.
28. (b) Januszkiewicz, K. R.; Alper, H. Organometallics 1983, 2, 1055.
29. (c) Blum, J.; Amer, I.; Zoran, A.; Sasson, Y. Tetrahedron Lett. 1983, 24, 4139.
30. (d) Schulz, J.; Roucoux, A.; Patin, H. J. Chem. Soc., Chem. Commun. 1999, 535.
31. (e) Stuhl, L. S.; Rakowski DuBois, M.; Hirsekorn, F. J.; Bleeke, J. R.; Stevens, A. E.; Muetterties, E. L. J. Am. Chem. Soc. 1978, 100, 2405.
32. (a) Pieta, D.; Trzeciak, A. M.; Ziólkowski, J. J. J. Mol. Catal. 1983, 18, 193.
33. (b) Bennett, M. A.; Huang, T. N.; Smith, A. K.; Turney, T. W. J. Chem. Soc., Chem. Commun. 1978, 582.
34. (c) Russell, M. J.; White, C.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1977, 427.
35. (d) Bennett, M. A.; Huang, T. N.; Turney, T. W. J. Chem. Soc., Chem. Commun. 1979, 312.
36. (e) Lapporte, S. J.; Schuett, W. R. J. Org. Chem. 1963, 28, 1947.
37. (f) Fidalgo, E. G.; Plasseraud, L.; Süss-Fink, G. J. Mol. Catal. A: Chem. 1998, 132, 5.
38. (g) Ward, M. D.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 5253.
39. (h) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. J. Chem. Soc., Chem. Commun. 1999, 25.
40. (i) Plasseraud, L.; Süss-Fink, G. J. Organomet. Chem., 1997, 539, 163.
41. (a) Gao, H.; Angelici, R. J. J. Am. Chem. Soc. 1997, 119, 6937.
42. (b) Gao, H.; Angelici, R. J. Organometallics 1999, 18, 989.
43. (a) Gao, H.; Angelici, R. J. New J. Chem. 1999, 23, 633.
44. (b) Gao, H.; Angelici, R. J. J. Mol. Catal. A: Chem. 1999, 145, 83.
45. (a) Yang, H.; Gao, H.; Angelici, R. J. Organometallics 1999, 18, 2285.
46. (b) Gao, H.; Angelici, R. J. J. Mol. Catal. A: Chem. 1999, 149, 63.
47. (a) Costella, L.; Zotto, A. D.; Mezzetti, A.; Zangrando, E.; Rigo, P. J. Chem. Soc., Dalton Trans. 1993, 3001.
48. (b) Braunstein, P.; Matt, D.; Dusausoy, Y. Inorg. Chem. 1983, 22, 2043.
49. (c) Linder, E.; Schober, U. Inorg. Chem. 1988, 27, 212.
50. (d) Rigo, P. Inorg. Chim. Acta 1990, 44, L23.
51. (a) Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc., Dalton Trans. 1994, 2755.
52. (b) Anderson, M. P.; Casalnuovo, A. L.; Johnson, S. J.; Mattson, B. M.; Mueting, A. M.; Pignolet, L. H. Inorg. Chem. 1988, 27, 1649.
53. (c) Wang, H.-H.; Casalnuovo, A. L.; Johnson, B. L.; Mueting, A. M.; Pignolet, L. H. Inorg. Chem. 1988, 27, 325.
54. (a) Dholakia, S.; Gillard, R. D.; Wimmer, F. L. Polyhedron 1985, 4, 791.
55. (b) van Houten, J.; Watts, R. J. J. Am. Chem. Soc. 1976, 98, 1853.
56. (c) Wickramasinghe, W. A.; Bird, P. H.; Serpone, N. J. Chem. Soc., Chem. Commun. 1981, 1284.
57. (d) Kazlauskas, R. J.; Wrighton, M. S. J. Am. Chem. Soc. 1982, 104, 5784.
58. (e) Brown, A.; Howarth, O. W.; Moore, P.; Parr, W. J. E. J. Chem. Soc., Chem. Commun. 1977, 586.
59. Ahmed, I.; Parish, R. V. J. Organomet. Chem. 1993, 452, 23.
60. Giordano, G.; Crabtree, R. H. Inorg. Synth. 1990, 28, 88.
61. Bazant, V.; Chvalovsky, V.; Rathousky, J. Organosilicon Compounds; Academia: Prague, Czech Republic, 1965; Vol. 1, p 59.
62. Cocevar, C.; Mestroni, G.; Camus, A. J. Organomet. Chem. 1972, 35, 389.
63. (a) Narayanan, S.; Krishna, K. Appl. Catal. A 1996, 147, L253.
64. (b) Talukdar, A. K.; Bhattacharyya, K. G. Appl. Catal. A 1993, 96, 229.
65. (c) Mahata, N.; Vishwanathan, V. J. Mol. Catal. A: Chem. 1997, 120, 267.
66. (d) Mahata, N.; Vishwanathan, V. Catal. Today 1999, 49, 65.
67. (e) Srinivas, S. T.; Rao, P. K. J. Chem. Soc., Chem. Commun. 1993, 33.
68. (f) Gonzalez-Velasco, J. R.; Gonzalez, M. P.; Gutierrez-Ortiz, J. L.; Gutierrez-Ortiz, M. A. Ind. Eng. Chem. Res. 1995, 34, 1031.
69. Corma, A.; Iglesias, M.; Sáchez, F. Catal. Lett. 1995, 32, 313.
70. Okano, T.; Tsukiyama, K.; Konishi, H.; Kiji, J. Chem. Lett. 1982, 603.
71. (a) Conner, W. C., Jr.; Falconer, J. L. Chem. Rev. 1995, 95, 759.
72. (b) Roessner, F.; Roland, U. J. Mol. Catal A: Chem. 1996, 112, 401.
73. (c) Conner, W. C., Jr.; Pajonk, G. M.; Teichner, S. J. Adv. Catal. 1986, 34, 1.
74. (d) Rozanov, V. V.; Krylov, O. V. Russ. Chem. Rev. (Engl. Transl.) 1997, 66, 107.
75. Harman, W. D.; Taube, H., J. Am. Chem. Soc. 1988, 110, 7906.
76. (a) Lin, S. D.; Sanders, D. K.; Vannice, M. A. Appl. Catal. A 1994, 113, 59.
77. (b) Rajashekharam, M. V.; Bergault, I.; Fouilloux, P.; Schweich, D.; Delmas, H.; Chaudhari, R. V. Catal. Today 1999, 48, 83.
78. (c) Bergault, I.; Fouilloux, P.; Joly-Vuillemin, C.; Delmas, H. J. Catal. 1998, 175, 328.
79. (d) Masson, J.; Cividino, P.; Court, J. Appl. Catal. A 1997, 161, 191.
80. (e) Bergault, I.; Joly-Vuillemin, C.; Fouilloux P.; Delmas, H. Catal. Today 1999, 48, 161.
81. (f) Masson, J.; Vidal, S.; Cividino, P.; Fouilloux, P.; Court, J. Appl. Catal. A 1993, 99, 147.
82. (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199.
83. (b) Barbaro, P.; Bianchini, C.; Togni, A. Organometallics 1997, 16, 3004.
84. (c) Yang, H.; Lugan, N.; Mathieu, R. J. Chem. Soc., Chem. Commun. 1995, 1721; Organometallics 1997, 16, 1401.
85. (c) Yang, H.; Lugan, N.; Mathieu, R. J. Chem. Soc., Chem. Commun. 1995, 1721; Organometallics 1997, 16, 1401.
86. (d) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087.
87. (e) Chan, A. S. C.; Landis, C. R. J. Mol. Catal. 1989, 49, 165.
88. (f) Wang, G. Z.; Backvall, J. E. J. Chem. Soc., Chem. Commun. 1992, 337.