Catalytic Conversions in Water. Part 21: Mechanistic Investigations on the Palladium-Catalysed Aerobic Oxidation of Alcohols in Water

Advanced Synthesis and Catalysis

Volumn 344, Issue 3-4, 2002, Pages 355-369

  Ten Brink, Gerd Jan ^a   Arends, Isabel W C E ^a   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Alcohols; Kinetics; Oxidation; Palladium; Water as solvent

Indexed keywords

EID: 0010472440     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200206)344:3/4<355::AID-ADSC355>3.0.CO;2-S     Document Type: Article

References (139)

1. Ullmann's encyclopedia of industrial organic chemistry, VCH, Weinheim.
2. a) G. Cainelli, G. Cardillo, Chromium Oxidants in Organic Chemistry, Springer, Berlin, 1984;
3. b) S. V. Ley, A. Madin, in Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming, S. V. Ley), Pergamon, Oxford, 1991, Vol. 7, pp. 251.
4. R. A. Sheldon, Top. Curr. Chem. 1993, 164, 21-43.
5. a) B. M. Trost, Science 1991, 254, 1471-1477;
6. b) B. M. Trost, Angew. Chem. 1995, 107, 285-303; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
7. b) B. M. Trost, Angew. Chem. 1995, 107, 285-303; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
8. a) J.-E. Bäckvall, R. L. Chowdhury, U. Karlsson, J. Chem. Soc. Chem. Commun. 1991, 473-475;
9. b) E. Gómez-Bengoa, P. Noheda, A. M. Echavarren, Tetrahedron Lett. 1994, 35, 7097-7098.
10. K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189.
11. T. Mukaiyama, in The Activation of Dioxygen and Homogeneous Catalytic Oxidation, (Eds.: D. H. R. Barton, A. E. Bartell, D. T. Sawyer), Plenum, New York, 1993, pp. 133-146.
12. a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetrahedron Lett. 1998, 39, 6011-6014;
13. b) T. Nishimura, K. Ohe, T. Onoue, S. Uemura, J. Org. Chem. 1999, 64, 6750-6755;
14. c) N. Kakiuchi, T. Nishimura, M. Inoue, S. Uemura, Bull. Chem. Soc. Jpn. 2001, 74, 165-172;
15. d) T. Nishimura, K. Ohe, S. Uemura, J. Am. Chem. Soc. 1999, 121, 2645-2646;
16. e) T. Nishimura, Y. Maeda, N. Kakiuchi, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 4301-4305;
17. f) T. Nishimura, N. Kakiuchi, T. Onoue, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 1915-1918.
18. a) V. Bellosta, R. Benhaddou, S. Czernecki, Synlett 1993, 861-863;
19. b) H. Nagashima, K. Sato, J. Tsuji, Tetrahedron 1985, 41, 5645-5651;
20. c) K. Hallman, C. Moberg, Adv. Synth. Catal. 2001, 343, 260-263.
21. a) R. Bortolo, D. Bianchi, R. D'Aloisio, C. Querci, M. Ricci, J. Mol. Catal. A Chem. 2000, 153, 25-29;
22. b) R. Bortolo, R. D'Aloisio, D. Bianchi, S. Soattini, C. Querci, EP 0853064, 1997; Chem. Abstr. 1998, 129, P110928y.
23. a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Science 1996, 274, 2044-2046;
24. b) Y. Nagata, C. Miyamoto, Y. Matsushima, S. Matsumoto, Chem. Pharm. Bull. 2000, 48, 71-76;
25. c) B. Betzemeier, M. Cavazzini, S. Quici, P. Knochel, Tetrahedron Lett. 2000, 41, 4343-4346.
26. a) T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2000, 65, 6502-6507;
27. b) T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 1995, 36, 6923-6926.
28. a) C. Bilgrien, S. Davis, R. S. Drago, J. Am. Chem. Soc. 1987, 109, 3786-3787;
29. b) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, S. M. Brown, J. Am. Chem. Soc. 1997, 119, 12661-12662;
30. c) A. Hanyu, E. Takezawa, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1998, 39, 5557-5560;
31. d) R. Lenz, S. V. Ley, J. Chem. Soc. Perkin Trans. 1 1997, 3291-3292;
32. e) B. Hinzen, R. Lenz, S. V. Ley, Synthesis 1998, 977-979;
33. f) A. Dijksman, A. Marino-Gonzalez, A. Mairata I Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826-6833;
34. g) M. Matsumoto, S. Ito, Synth. Commun. 1984, 14, 697-700;
35. h) K. Masutani, T. Uchida, R. Irie, T. Katsuki, Tetrahedron Lett. 2000, 41, 5119-5123.
36. T. Mallat, A. Baiker, Catal. Today 1994, 19, 247-284.
37. H. Fiege, K. Wedemeyer, Angew. Chem. 1981, 93, 812-813; Angew. Chem. Int. Ed. Engl. 1981, 20, 783-784.
38. H. Fiege, K. Wedemeyer, Angew. Chem. 1981, 93, 812-813; Angew. Chem. Int. Ed. Engl. 1981, 20, 783-784.
39. G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639.
40. a) K. Zaw, P. M. Henry, Organometallics 1992, 11, 2008-2015;
41. b) K. Zaw, M. Lautens, P. M. Henry, Organometallics 1985, 4, 1286-1291;
42. c) K. Zaw, P. M. Henry, J. Org. Chem. 1990, 55, 1842-1847.
43. a) A. V. Nikiforova, I. I. Moiseev, Ya. K. Syrkin, Russ. J. Gen. Chem. 1963, 33, 3166-3169;
44. b) I. V. Kozhevnikov, V. E. Taraban'ko, K. I. Matveev, Kinet. Catal. 1980, 21, 679-684;
45. c) J. J. Berzelius, Justus Liebigs Ann. Chem. 1828, B13, 435.
46. Data obtained from J. Phys. Chem. Ref. Data 1982, 11, suppl. 2.
47. A. A. Ketterling, A. S. Lisitsyn, A. V. Nosov, V. A. Likholobov, Appl. Catal. A 1990, 66, 123-132.
48. R. A. T. M. van Benthem, H. Hiemstra, P. W. N. M. vanLeeuwen, J. W. Geus, W. N. Speckamp, Angew. Chem. 1995, 107, 500-503; Angew. Chem. Int. Ed. Engl. 1995, 34, 457-460.
49. R. A. T. M. van Benthem, H. Hiemstra, P. W. N. M. vanLeeuwen, J. W. Geus, W. N. Speckamp, Angew. Chem. 1995, 107, 500-503; Angew. Chem. Int. Ed. Engl. 1995, 34, 457-460.
50. a) E. Alessio, G. Mestroni, J. Organometal. Chem. 1985, 291, 117-127;
51. b) P. Wehman, PhD thesis, University of Amsterdam, 1995.
52. a) P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741-2769;
53. b) R. A. Klein, P. Witte, R. van Beizen, J. Fraanje, K. Goubitz, M. Numan, H. Schenk, J. M. Ernsting, C. J. Elsevier, Eur. J. Inorg. Chem. 1998, 319-330.
54. BIMIP [or: 2,2′-bis(diphenylphosphino)-1,1-bibenzimidazole]: P. Antognazza, T. Benincori, S. Mazzoli, F. Sannicolo, T. Pilati, Phosphorus, Sulphur and Silicon and Related Elements 1999, 146, 405-408.
55. G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62; Angew. Chem. Int. Ed. Engl. 1967, 9, 92.
56. G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62; Angew. Chem. Int. Ed. Engl. 1967, 9, 92.
57. G.-J. ten Brink, G. Papadogianakis, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 1998, 2359-2360.
58. I. I. Moiseev, M. N. Vargaftik, Ya. K. Syrkin, Dokl. Akad. Nauk. SSSR 1960, 133, 377-380.
59. A. I. Roshchin, S. M. Kel'chevski, N. A. Bumagin, J. Organometal. Chem. 1998, 560, 163-167.
60. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
61. G.-J. ten Brink, G. Papadogianakis, I. W. C. E. Arends, R. A. Sheldon, Appl. Catal. A 2000, 194-195, 435-442.
62. a) U. Fekl, R. van Eldik, C. Richardson, W. T. Robinson, Inorg. Chem. 2001, 40, 3247-3251;
63. b) S. Kannan, A. J. James, P. R. Sharp, Polyhedron 2000, 19, 155-163;
64. c) G. Sánchez, A. Sanmartín, J. García, G. López, Transition Met. Chem. 1997, 22, 545-548;
65. d) G. Sánchez, J. L. Serrano, M. C. Ramírez de Arellano, J. Pérez, G. López, Polyhedron, 2000, 19, 1395-1406.
66. a) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475;
67. b) A. Fujii, E. Hagiwara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458;
68. c) B. Longato, G. Pilloni, G. Valle, B. Corain, Inorg. Chem. 1988, 27, 956-958;
69. d) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
70. S. Wimmer, P. Castan, F. L. Wimmer, N. P. Johnson, J. Chem. Soc. Dalton Trans. 1989, 403-412.
71. K. Kaneda, M. Fujii, K. Morioka, J. Org. Chem. 1996, 61, 4502-4503.
72. M. K. Starchevsky, S. L. Hladiy, Y. A. Pazdersky, M. N. Vargaftik, I. I. Moiseev, J. Mol. Catal. A Chem. 1999, 146, 229-236.
73. P. M. Maitlis, The Organic Chemistry of Palladium 2, Academic Press, New York, 1971, pp. 119.
74. M. N. Vargaftik, V. P. Zagoradnikov, I. I. Moiseev, Kinet. Catal. 1981, 22, 743-746.
75. I. V. Kozhevnikov, V. E. Taraban'ko, K. I. Matveev, Kinet. Catal. 1980, 21, 679-684.
76. 2+ disappeared, an induction period was observed, and the reactivity of the alcohols tested followed the mobility order of the α-hydrogen in C-H activation by platinum metals: a) V. B. Ukraintsev, V. V. Potekhin, Russ. J. Gen. Chem. 1997, 67, 1509-1512; b) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987.
77. 2+ disappeared, an induction period was observed, and the reactivity of the alcohols tested followed the mobility order of the α-hydrogen in C-H activation by platinum metals: a) V. B. Ukraintsev, V. V. Potekhin, Russ. J. Gen. Chem. 1997, 67, 1509-1512; b) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987.
78. S. Wimmer, P. Castan, F. L. Wimmer, N. P. Johnson, Inorg. Chim. Acta 1988, 142, 13-15.
79. S. G. Fox, R. D. Gillard, Polyhedron 1988, 7, 349-352.
80. a) R. H. Crabtree, Chem. Rev. 1995, 95, 987-1007;
81. b) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932;
82. c) J. K. Beattie, S. Macleman, A. F. Masters, Inorg. Chim. Acta 1999, 294, 99-102;
83. d) C. Shen, E. A. Garcia-Zayas, A. Sen, J. Am. Chem. Soc. 2000, 122, 4029-4031.
84. H. E. Bryndza, L. K. Fong, R. A. Paciello, W. Tam, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 1444-1456.
85. R. Jira, in Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, pp. 374-393.
86. a) R. M. Barter, J. S. Littler, J. Chem. Soc. (B) 1967, 205-210;
87. b) J. S. Littler, J. Chem. Soc. 1962, 2190-2197;
88. c) R. Brownell, A. Leo, Y. W. Chang, F. H. Westheimer, J. Am. Chem. Soc. 1960, 82, 406-410.
89. 3-methallyl-palladium complex: V. V. Potekhin, N. K. Skvortso, N. G. Antonov, V. K. Bel'skii, V. B. Ukraintsev, Russ. J. Gen. Chem. 1997, 67, 1155-1158.
90. For a review on oxidation of tertiary alcohols, see: K. Wietzerbin, J. Bernadou, B. Meunier, Eur. J. Inorg. Chem. 2000, 1391-1406.
91. a) H. E. Bryndza, W. Tam, Chem. Rev. 1988, 88, 1163-1188;
92. b) J. A. Davies, F. R. Hartley, Chem. Rev. 1981, 81, 79-90;
93. c) T. Yoshida, T. Okano, S. Otsuka, J. Chem. Soc. Dalton Trans. 1976, 993-999.
94. W. K. Wan, K. Zaw, P. M. Henry, Organometallics 1988, 7, 1677-1683.
95. J. W. Francis, P. M. Henry, J. Mol. Catal. A Chem. 1995, 99, 77-86.
96. A. D. Ketley, L. P. Fisher, J. Organometal. Chem. 1968, 13, 243-248.
97. J. S. Coe, P. L. Rispoli, J. Chem. Soc. Dalton Trans. 1976, 2215-2218.
98. H. D. Kaesz, R. B. Saillant, Chem. Rev. 1972, 72, 231-281.
99. N. Kiers, B. L. Feringa, H. Kooijman, A. L. Spek, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1992, 1169-1170.
100. Y.-J. Kim, K. Osakada, A. Takenaka, A. Yamamoto, J. Am. Chem. Soc. 1990, 112, 1096-1104.
101. a) M. E. Jung, L. M. Speltz, J. Am. Chem. Soc. 1976, 98, 7882-7884;
102. b) M. E. Jung, R. W. Brown, Tetrahedron Lett. 1978, 2771-2774.
103. a) T. E. Nalesnik, N. L. Holy, J. Org. Chem. 1977, 42, 372-374;
104. b) Y. Tamaru, Y. Yamada, K. Inoue, Y. Yamamoto, Z.-I. Yoshida, J. Org. Chem. 1983, 48, 1286-1292.
105. a) Isomerisation (transfer hydrogenation) of 2-ethyl-3-hydroxyhexanal to 2-ethyl-1-hydroxy-3-hexanone was not observed under our reaction conditions; b) the tungstate/hydrogen peroxide system of Noyori also showed a preference for secondary alcohol oxidation in the case of 2-ethyl-1,3-hexanediol: K. Sato, M. Aoki, J. Takagi, K. Zimmermann, R. Noyori, Bull. Chem. Soc. Jpn. 1999, 72, 2287-2306.
106. H. Tomioka, K. Takai, K. Oshima, H. Nozaki, Tetrahedron Lett. 1981, 22, 1605-1608.
107. Strictly speaking, this value was obtained in the oxidation of the bis(triphenylmethyl) ether.
108. K. Kaneda, Y. Fujie, K. Ebitani, Tetrahedron Lett. 1997, 38, 9023-9026.
109. a) I. I. Moiseev, M. N. Vargaftik, Russ. Chem. Rev. 1990, 59, 1133-1149;
110. b) I. P. Stolyarov, M. N. Vargaftik, I. I. Moiseev, Kinet. Catal. 1987, 28, 1172-1177.
111. NB: this value is the sum of the primary and secondary isotope effects. The contribution from the primary isotope effect is expected to be higher than 1.8 ± 0.1 therefore.
112. H. B. Charman, J. Chem. Soc. (B) 1967, 629-632.
113. G. Noronha, P. M. Henry, J. Mol. Catal. A Chem. 1997, 120, 75-87.
114. H. Kwart, Acc. Chem. Res. 1982, 15, 401-408.
115. E. V. Stern, in Transition Metals in Homogeneous Catalysis, (Ed.: G. N. Schrauzer), Dekker, New York, 1971, pp. 93-146.
116. A. Dobson, S. D. Robinson, J. Organometal. Chem. 1975, 87, C52-C53.
117. B. R. James, Homogeneous Hydrogenation, Wiley Interscience, New York, 1973.
118. a) P. M. Maitlis, The Organic Chemistry of Palladium 1, Academic Press, New York, 1971, pp. 103-105;
119. b) R. F. Jones, J. R. Fisher, D. J. Cole-Hamilton, J. Chem. Soc. Dalton Trans. 1981, 2550-2555.
120. I. I. Moiseev, M. N. Vargaftik, in Catalysis with Di-and Polynuclear Metal Cluster Complexes, (Eds.: R. D. Adams, F. A. Cotton), Wiley-VCH, New York, 1998, pp. 395-442.
121. T. Hosokawa, S.-I. Murahashi, Acc. Chem. Res. 1990, 23, 49-54.
122. a) C. J. Nyman, C. E. Wymore, G. Wilkinson, J. Chem. Soc. (A) 1968, 561-563;
123. b) R. A. Sheldon, J. A. van Doorn, J. Organometal. Chem. 1975, 94, 115-129;
124. c) S. Muto, H. Ogata, Y. Kamiya, Chem. Lett. 1975, 8, 809-812.
125. S. S. Stahl, J. L. Thorman, R. C. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188-7189.
126. F. Igersheim, H. Mimoun, Nouv. J. Chim. 1980, 4, 711-713.
127. A. S. Berenblyum, S. L. Mund, T. P. Goranskaya, I. I. Moiseev, Izv. Akad. Nauk. SSSR, Ser. Khim. 1980, 8, 1948-1949.
128. I. V. Kozhevnikov, V. E. Taraban'ko, K. I. Matveev, Kinet. Catal. 1981, 21, 685-690.
129. E. Sinn, K. Matthes, E. Naumann, Wiss. Z. Friedrich Schiller Univ. Jena, Math.-Naturwiss. Reihe 1967, 16, 523-529.
130. 2-AMS=2-anthraquinone monosulfonate, 1,5-ADS= 1,5-anthraquinone disulfonate.
131. W. M. Clark, Oxidation/Reduction Potentials of Organic Systems, Williams & Wilkins, Baltimore, 1960.
132. M. Freifelder, J. Org. Chem. 1964, 29, 2895-2898.
133. a) B. Helferich, K. G. Kleb, Liebigs Ann. 1960, 635, 91-96;
134. b) B. Helferich, V. Böllert, Chem. Ber. 1961, 94, 505-509.
135. A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Synlett 2001, 102-104.
136. M. Yamada, Y. Tanaka, Y. Yoshimoto, S. Kuroda, I. Shimao, Bull. Chem. Soc. Jpn. 1992, 65, 1006-1011.
137. G. E. Inglett, G. F. Smith, J. Am. Chem. Soc. 1950, 72, 842-844.
138. J. Mlochowski, Z. Szulc, Pol. J. Chem. 1983, 57, 33-39.
139. W. A. Herrmann, W. R. Thiel, J. G. Kuchler, Chem. Ber. 1990, 123, 1953-1961.