Pyrazole and trispyrazolylmethane rhenium complexes as catalysts for ethane and cyclohexane oxidations

Applied Catalysis A: General

Volumn 317, Issue 1, 2007, Pages 43-52

  Alegria, Elisabete C B ^a,b   Kirillova, Marina V ^a   Martins, Luísa M D R S ^a,b   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

Author keywords

Alkanes; Cyclohexane; Ethane; Functionalization; Homogeneous catalysis; Oxidation; Rhenium

Indexed keywords

ACETIC ACID; COMPLEXATION; ETHANE; METHANE; POTASSIUM COMPOUNDS; RHENIUM COMPOUNDS;

ACETALDEHYDES; CYCLOHEXANE OXIDATIONS; FUNCTIONALIZATION; HOMOGENEOUS CATALYSIS; PROPIONIC ACIDS; PYRAZOLE COMPLEXES;

CATALYSTS;

EID: 33845539125     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2006.09.038     Document Type: Article

References (109)

1. Shilov A.E., and Shul'pin G.B. Chem. Rev. 97 (1997) 2879
2. Shul'pin G.B. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis. second ed. vol. 2 (2004), Wiley-VCH, New York 215-242
3. Shilov A.E., and Shul'pin G.B. Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes (2000), Kluwer Academic Publisher, Dordrecht
4. Shul'pin G.B. Comptes Rendus. Chimie 6 (2003) 163
5. Jia C., Kitamara T., and Fujiwara Y. Acc. Chem. Res. 34 (2001) 633
6. Crabtree R.H. J. Chem. Soc. Dalton Trans. (2001) 2437
7. Labinger J.A., and Bercaw J.E. Nature 417 (2002) 507
8. In: Derouane E.G., Haber J., Lemos F., Ramôa Ribeiro F., and Guinet M. (Eds). Catalytic Activation and Functionalization of Light Alkanes, NATO ASI Series vol. 44 (1998), Kluwer Academic Publisher, Dordrecht
9. In: Hill C.L. (Ed). Activation and Functionalization of Alkanes (1995), Wiley, New York
10. Nizova G.V., Süss-Fink G., Stanislas S., and Shul'pin G.B. J. Chem. Soc. Chem. Commun. (1998) 1885
11. Lin M., and Sen A. Nature 368 (1994) 613
12. Lin M., and Sen A. J. Chem. Soc. Chem. Commun. (1992) 892
13. Bagno A., Bukala J., and Olah G.A. J. Org. Chem. 55 (1990) 4284
14. Taniguchi Y., Hayashida T., Shibasaki H., Piao D.G., Kitamura T., Yamaji T., and Fujiwara Y. Org. Lett. 1 (1999) 557
15. Nishiguchi T., Nakata K., Takaki K., and Fujiwara Y. Chem. Lett. (1992) 1141
16. Kitamura T., Ishida Y., Yamaji T., and Fujiwara Y. Bull. Chem. Soc. Jpn. 76 (2003) 1677
17. Asadullah M., Taniguchi Y., Kitamura T., and Fujiwara Y. Appl. Catal. A 443 (2000) 194
18. Asadullah M., Kitamura T., and Fujiwara Y. Angew. Chem. 112 (2000) 2609
19. Asadullah M., Kitamura T., and Fujiwara Y. Appl. Organomet. Chem. 13 (1999) 539
20. Asadullah M., Kitamura T., and Fujiwara Y. Chem. Lett. (1999) 449
21. Yin G.C., Piao D.G., Kitamura T., and Fujiwara Y. Appl. Organomet. Chem. 14 (2000) 438
22. Piao D., Inoue K., Shibasaki H., Taniguchi Y., Kitamura T., and Fujiwara Y. J. Organomet. Chem. 574 (1999) 116
23. Reis P.M., Silva J.A.L., Palavra A.F., da Silva J.J.R.F., Kitamura T., Fujiwara Y., and Pombeiro A.J.L. Angew. Chem. Int. Ed. 42 (2003) 821
24. Periana R.A., Mironov O., Taube D., Bhalla G., and Jones C.J. Science 301 (2003) 814
25. Tersier L., Bordes E., and Gubelmann-Bonneau M. Catal. Today 24 (1995) 335
26. Nowinska K., Sopa M., and Szuba D. Catal. Lett. 39 (1996) 275
27. Wang Y., and Otsuka K. J. Catal. 171 (1997) 106
28. Ueda W., and Oshira K. Appl. Catal. A: Gen. 200 (2000) 135
29. Süss-Fink G., Gonzalez L., and Shul'pin G.B. Appl. Catal. A: Gen. 217 (2001) 111
30. Shul'pin G.B., Süss-Fink G., and Shul'pina L.S. J. Chem. Res. (2000) 576
31. Shibamoto A., Sakaguchi S., and Ishii Y. Tetrahedron Lett. 43 (2002) 8859
32. Linke D., Wolf D., Baerns M., Timpe O., Schlogl R., Zeyss S., and Dingerdissen U. J. Catal. 205 (2002) 16
33. Linke D., Wolf D., Baerns M., Zeyss S., and Dingerdissen U. J. Catal. 205 (2002) 32
34. Kirillov A.M., Haukka M., Kirillova M.V., and Pombeiro A.J.L. Adv. Synth. Catal. 347 (2005) 1435
35. Asadullah M., Kitamura T., and Fujiwara Y. J. Catal. 195 (2000) 180
36. Asadullah M., Taniguchi Y., Kitamura T., and Fujiwara Y. Tetrahedron Lett. 40 (1999) 8867
37. Nakata K., Yamaoka Y., Miyata T., Taniguchi Y., Takaki K., and Fujiwara Y. J. Organomet. Chem. 473 (1994) 329
38. Anisia K.S., and Kumar A. Appl. Catal. A: Gen. 273 (2004) 193
39. Ullmann's Encyclopedia of Industrial Chemistry, sixth ed., Wiley-VCH, Weinheim, 2002.
40. Weissermel W., and Horpe H.J. Ind. Org. Chem. second ed. (1993), VCH Press, Weinheim
41. Schuchardt U., Cardoso D., Sercheli R., Pereira R., da Cruz R.S., Guerreiro M.C., Mandelli D., Spinacé E.V., and Pires E.L. J. Appl. Catal. A: Gen. 211 (2001) 1
42. Schuchardt U., Mandelli D., and Shul'pin G.B. Tetrahedron Lett. 37 (1996) 6487
43. Shul'pin G.B., Nizova G.V., Kozlov Y.N., Cuervo L.G., and Süss-Fink G. Adv. Synth. Catal. 346 (2004) 317
44. Reis P.M., Silva J.A.L., da Silva J.J.R.F., and Pombeiro A.J.L. Chem. Commun. (2000) 1845
45. Kopylovich M.N., Kirillov A.M., Baev A.K., and Pombeiro A.J.L. J. Mol. Catal. A: Chem. 206 (2003) 163
46. Kirillov A.M., Kopylovich M.N., Kirillova M.V., Karabach E.Y., Haukka M., da Silva M.F.C.G., and Pombeiro A.J.L. Adv. Synth. Catal. 348 (2006) 159
47. Kirillov A.M., Haukka M., da Silva M.F.C.G., and Pombeiro A.J.L. Eur. J. Inorg. Chem. (2005) 2071
48. Shul'pin G.B. J. Mol. Catal. A: Chem. 189 (2002) 39
49. Shul'pin G.B., and Nizova G.V. React. Kinet. Catal. Lett. 48 (1992) 333
50. Shul'pin G.B., Attanasio D., and Suber L. J. Catalysis 142 (1993) 147
51. Owens G.S., Árias J., and Abu Omar M.M. Catal. Today 55 (2000) 317
52. Romão C.C., Kühn F.E., and Herrmann W.A. Chem. Rev. 97 (1997) 213
53. Santos A.M., Romão C.C., and Kühn F.E. J. Am. Chem. Soc. 125 (2003) 2414
54. Bough A.O., and Espenson J.H. J. Mol. Catal. A: Chem. 200 (2003) 43
55. Sharma V.B., Jain S.L., and Sain B. Tetrahedron Lett. 44 (2003) 3235
56. Lahti D.W., and Espenson J.H. Inorg. Chem. 39 (2000) 2164
57. Jeon H.J., and Nguyen S.T. Chem. Commun. (2001) 235
58. Hermann W.A., and Kühn F.E. Acc. Chem. Res. 30 (1997) 169
59. Hermann W.A., Kuchler J.G., Felixberger J.K., Herdtweck E., and Wagner W. Angew. Chem. Int. Ed. 27 (1988) 394
60. Herrmann W.A., Kühn F.E., Fischer R.W., Thiel W.R., and Romão C.C. Inorg. Chem. 31 (1992) 4431
61. Herrmann W.A., Fischer R.W., and Marz D.W. Angew. Chem. Int. Ed. 30 (1991) 1638
62. Bernini R., Mincione E., Cortese M., Saladino R., Gualandi G., and Belfiore M.C. Tetrahedron Lett. 44 (2003) 4823
63. Goti A., and Nannelli L. Tetrahedron Lett. 37 (1996) 6025
64. Zauche T.H., and Espenson J.H. Inorg. Chem. 36 (1997) 5257
65. Soldani G., Cardona F., and Goti A. Tetrahedron Lett. 44 (2003) 5589
66. Herrmann W.A., Fischer R.W., and Correia J.D.G. J. Mol. Catal. A: Chem. 94 (1994) 213
67. Bernini R., Coratti A., Fabrizi G., and Goggiamani A. Tetrahedron Lett. 44 (2003) 8991
68. Pombeiro A.J.L., da Silva M.F.C.G., and Crabtree R.H. In: King R.B. (Ed). Encyclopedia of Inorganic Chemistry vol. IX (2005), Wiley 5499-5515
69. Romão C. In: King R.B. (Ed). Encyclopedia of Inorganic Chemistry vol. VII (2005), Wiley 4647-4692
70. Pettinari C., and Santini C. In: McCleverty J.A., and Meyer T.J. (Eds). Comprehensive Coordination Chemistry II vol. I (2004), Elsevier, Oxford 159-210
71. Trofimenko S. Polyhedron 23 (2004) 197
72. Pettinari C., and Pettinari R. Coord. Chem. Rev. 249 (2005) 525
73. Trofimenko S. Scorpionates-The Coordination Chemistry of Poly(pyrazolyl) borate Ligands (1999), Imperial College, London
74. MacDonald M.G., Kostelansky C.N., White P.S., and Templeton J.L. Organometallics 25 (2006) 4560
75. Chatt J., Dilworth J.R., Leigh G.J., and Gupta V.D. J. Chem. Soc. (1971) 2631
76. Alegria E.C.B., Martins L.M.D.R.S., da Silva M.F.C.G., and Pombeiro A.J.L. J. Organomet. Chem. 690 (2005) 1947
77. Parshall G.W. Inorg. Synth. 17 (1977) 110
78. Chatt J., and Row A.G. J. Chem. Soc. (1962) 4019
79. G.S. Mishra, E.C.B. Alegria, L.M.D.R.S. Martins, A.J.L. Pombeiro, in preparation.
80. Alegria E.C.B., Martins L.M.D.R.S., Haukka M., and Pombeiro A.J.L. Dalton Trans. 41 (2006) 4954
81. Lever B.P. Inorg. Chem. 30 (1991) 1980
82. http://www.chem.yorku.ca/profs/lever/elparam98.htm.
83. Carvalho M.F.N.N., Duarte M.T., Galvão A.M., and Pombeiro A.J.L. J. Organometal. Chem. 469 (1994) 79
84. J. Chatt, C.T. Kan, G.J. Leigh, H. Neukomm, C.J. Pickett, D.R. Stanley, J.C.S. Dalton (1980) 2032.
85. Pombeiro A.J.L. In: Scholz F., Pickett C.J., Bard A.J., and Stratmann M. (Eds). Encyclopedia of Electrochemistry vol. 7 (2006), Wiley-VCH 77-108 (inorganic chemistry)
86. Pombeiro A.J.L. J. Organometal. Chem. 690 (2005) 6021
87. Poltowicz J., and Haber J. J. Mol. Catal. A: Chem. 220 (2004) 43
88. Yin C., Pião D.G., Kitamura T., and Fujiwara Y. Appl. Organomet. Chem. 14 (2000) 438
89. Hermann W.A., Fischer R.W., Scherer W., and Rauch M.U. Angew. Chem. Int. Ed. 105 (1993) 1209
90. Adam W., Hermann W.A., Lin J., Saha-Möller C.R., Fischer R.W., and Correia J.D.G. Angew. Chem. Int. Ed. 106 (1994) 2545
91. Hermann W.A., Correia J.D.G., Kühn F.E., Artus G.R.J., and Romão C.C. Chem. Eur. J. 2 (1996) 2
92. Khaliullin R.Z., Bell A.T., and Head-Gordon M. J. Phys. Chem. B 109 (2005) 17984
93. Koslov Yu.N., Nizova G.V., and Shul'pin G.B. Russ. J. Phys. Chem. 75 (2001) 770
94. Shul'pin G.B., Kozlov Yu.N., Nizova G.V., Süss-Fink G., Stanislas S., Kitaygorodskiy A., and Kulikova V.S. J. Chem. Soc., Perkin Trans. 2 (2001) 1351
95. Süss-Fink G., Stanislas S., Shul'pin G.B., Nizova G.V., Stoeckli-Evans H., Neels A., Bobillier C., and Claude S. J. Chem. Soc., Dalton Trans. (1999) 3169
96. Nicholson T., and Zubieta J. Inorg. Chim. Acta 134 (1987) 191
97. Mishra G.S., and Pombeiro A.J.L. J. Mol. Catal. A: Chem. 239 (2005) 96
98. Mishra G.S., and Pombeiro A.J.L. Appl. Catal. A: Gen. 304 (2006) 185
99. Shul'pin G.B., Süss-Fink G., and Smith J.R.L. Tetrahedron 55 (1999) 5345
100. Shul'pin G.B., and Suss-Fink G. J. Chem. Soc. Perkin Trans. 2 (1995) 1459
101. Mimoun H., Saussine L., Daire E., Postel M., Fischer J., and Weiss R. J. Am. Chem. Soc. 105 (1983) 3101
102. Goldstein A.S., Beer R.H., and Draggo R.S. J. Am. Chem. Soc. 116 (1994) 2424
103. Ito S., Okuno T., Matsushima H., Tokii T., and Nishida Y. J. Chem. Soc., Dalton Trans. (1996) 4479
104. Okuno T., Ohba S., and Nishida Y. Polyhedron 16 (1997) 3765
105. Nishino S., Hosomi H., Ohba S., Matsushima H., Tokii T., and Nishida Y. J. Chem. Soc., Dalton Trans. (1997) 354
106. Reis P.M., da Silva J.A.L., da Silva J.J.R.F., and Pombeiro A.J.L. J. Mol. Catal. A: Chem. 224 (2004) 189
107. Kirillov A.M., Kopylovich M.N., Kirillova M.V., Haukka M., da Silva M.F.C.G., and Pombeiro A.J.L. Angew. Chem. Int. Ed. 44 (2005)
108. Moiseev I.I., Shishkin D.I., and Gekhman A.E. New J. Chem. 23 (1989) 682
109. Hogan T., and Sen A. J. Am. Chem. Soc. 119 (1997) 2642