Synthetic applications of the palladium-catalyzed oxidation of olefins to ketones

Synthesis (Germany)

Volumn 1984, Issue 5, 1984, Pages 369-384

  Tsuji, Jiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85083243520     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1984-30848     Document Type: Review

References (118)

1. J. Smidt, et al., Angew. Chem. 71, 176 (1959).
2. J. Smidt et al., Angew. Chem. 74, 93 (1962).
3. J. Tsuji, Organic Synthesis with Palladium Compounds, Springer Verlag, Berlin, 1980.
4. W.H. Clement, C.M. Selwitz, .J. Org. Chem. 29, 241 (1964).
5. W.G. Lloyd, B.J. Luberoff, J. Org. Chem. 34, 3949 (1969).
6. D.R. Fahey, E.A. Zuech, J. Org. Chem. 39, 3276 (1974).
7. F.J. McQuillin, D.G. Parker. .J. Chem. Soc. Perkin Trans. I 1974, 809.
8. R. Jira, W. Freiesleben. Organometal. React. 3, 1 (1972).
9. P.M. Henry, Adv. Organometal. Chem. 13, 363 (1975).
10. P.M. Henry, Ace. Chem. Res. 6, 16 (1973).
11. A. Aguilo, Adv. Organometal Chem. 5, 321 (1967).
12. E.W. Stern, Catal. Rev. 1, 73 (1968).
13. A. P. Kozikowski, H.F. Wetter, Synthesis 1976, 561.
14. P.M. Maitlis, The Organic Chemistry of Palladium, Vol. 2, Academic Press, New York, 1971.
15. P. M. Henry, Palladium Catalyzed Oxidation of Hydrocarbons, D. Reidal Publishing Co., Dordrecht, Holland, 1980.
16. H. Mimoun, J. Mol. Catal. 7, 1 (1980).
17. J. Tsuji, I. Shimizu, K. Yamamoto, Tetrahedron Lett. 1976, 2975.
18. M. Kolb, E. Bratz, K. Dialer, J. Mol. Catal. 2, 399 (1977).
19. C. Lapinte, H. Riviere, Tetrahedron Lett. 1977, 3817.
20. N.T. Byrom, R. Grigg, B. Kongkathip, J. Chem. Soc. Chem. Commun. 1976, 216.
21. M. Hrusovsky, M. Cihova, V. Laton, 'Zb. Pr. Chemickotechnol. Fak. SVSTW1X, 161; C.A. 76, 33736 (1972).
22. J. Urbanec, M. Hrusovsky, M. Strasak. Petrochemia 16, 132 (1976); C.A. 87, 5123 (1977).
23. R. H. Lasco, German Patent (DOS) 2515 074, Diamond Shamrock Corp. (1975); C.A. 84, 4484 (1976).
24. R.H. Lasco, German Patent (DOS) 2515073, Diamond Shamrock Corp. (1975); C.A. 84, 16756 (1976). Japanese Patent 8207439, Asahi Chem. Ind. (1982); C.A. 96, 162158 (1982).
25. A. Kaszonyi, J. Vojtko, M. Hrusovsky, Collect. Czech. Chem. Commun. 47, 2128 (1982).
26. M. Cihova et al., Petrochemia 21, 72 (1981); C.A. 96, 103574 (1982).
27. j. Tsuji, I. Shimizu, Y. Kobayashi, Israel J. Chem., in press.
28. G.T. Rodeheaver, D.F. Hunt, J. Chem. Soc. Chem. Commun. 1971, 818.
29. D.F. Hunt, G.T. Rodeheaver, Tetrahedron Lett. 1972, 3595.
30. S. Uemura et al., J. Chem. Soc. Chem. Commun. 1971, 234.
31. P.M. Henry, J. Org. Chem. 32, 2575 (1967).
32. Stangl, R. Jira, Tetrahedron Lett. 1970, 3589.
33. M. Gouedard, F. Gaudemer, A. Gaudemer, Bull. Soc. Chim. Fr. 1973, 577.
34. M. Hrusovsky, J. Vojtko, M. Cihova, Hung. J. Ind. Chem. 2, 137 (1974); C.A. 82, 139205 (1975).
35. LI. Moiseev, M.N. Vargaftik, Y.K. Syrkin, Dokl. Akad. Nauk SSSR 133, 377 (1960); C.A. 54, 24350 (1960).
36. H.Arai, M. Yashiro, .J. Mol. Catal. 3, 427 (1977-78).
37. I. Moiseev, M.N. Vargaftik, Ya.K. Syrkin. Dokl. Akad. Nauk SSSR 130, 820 (1960); C.A. 54, 24350 (1960).
38. C.B. Cotterill, F. Dean, British Patent 941951, IC1 Ltd. (1963); C.A. 60, 4011 (1964).
39. M. Roussel, H. Mimoun, J. Org. Chem. 45, 5387 (1980).
40. J. Tsuji, H. Nagashima, K. Hori, Chem. Lett. 1980, 257.
41. H. Mimoun et al., .J. Am. Chem. Soc. 102, 1047 (1980).
42. B.S. Tovrog, F. Mares, S.E. Diamon, J. Am. Chem. Soc. 102, 6616 (1980).
43. A. Heumann, M. Reglier, B. Waegell, Angew. Chem. 91, 924-925 (1979); Angew. Chem. Int. Ed. Engl., 18, 866, 867 (1979).
44. A. Heumann, F. Chauvet, B. Waegell, Tetrahedron Lett. 23. 2767 (1982).
45. A. Andrews, K.P. Kelly, J. Am. Chem. Soc. 103, 2894 (1981).
46. K. I. Matveev et al., Kinet. Katal. 18, 380 (1977); C. A. 87, 22002 (1977).
47. M. Cihova et al., React. Kinet. Catal. Lett. 16, 383 (1981); C.A. 95, 168153 (1981).
48. H. Ogawa, H. Fujinami, K. Taya, J. Chem. Soc. Chem. Commun. 1981, 1274.
49. K. Urabe, J. Kimura, Y. Izumi, Shokubaill. 10 (1980); C.A. 95, 203263 (1981).
50. R. Hiittel, H. Christ, Chem. Ber. 96, 3101 (1963).
51. R. Hiittel, IL Christ, Chem. Ber. 97, 1439 (1964).
52. A. D. Ketley, J. Braatz, J. Chem. Soc. C'Hem. Commun. 1968, .
53. H.C. Volger, Reel. Trav. Chim. Pavs-Bas 88, 225 (1969).
54. R. Hiittel, M. McNiff, Chem. Ber. 106, 1789 (1973).
55. F. Conti et al., J. Organometal. Chem. 30, 421 (1971).
56. B.M. Trost. P.E. Strege, Tetrahedron Lett. 1974, 2603.
57. J. Tsuji, H. Nagashima, submitted to Organic Synthesis.
58. R.J. Thomas. K.N. Campbell, G.G. Hennion. J. Am. Chem. Soc. 60, 718 (1938).
59. H.C. Brown, P. Geoghegan Jr., J. Am. Chem. Soc. 89, 1522 (1967).
60. H. R. Rogers, J. Z. McDermott, G. M. Whitesides. J. Org. Chem. 40, 3577 (1975).
61. A. Zombeck, D. E. Hamilton, R. S. Drago, J. Am. Chem. Soc. 104. 6782 (1982).
62. F. Igersheim, H. Mimoun, J. Chem. Soc. Chem. Commun. 1978, 559.
63. F. Igersheim, H. Mimoun, Nouv. J. Chem. 4, 161 (1980).
64. H. Mimoun, M. M. P. Machirant, I. Seree de Roch, J. Am. Chem. Soc. 100, 5473 (1978).
65. W.G. Lloyd, .J. Org. Chem. 32, 2816 (1967).
66. T.E. Nalesnik, N.L. Holy, J. Org. Chem. 42, 372 (1977).
67. T.F. Blackburn, J. Schwartz. J. Chem. Soc. Chem. Commun. 1977, 157.
68. LV. Kozhevnikov, V.E. Taraban'ko, K. Matveev, Dokl. Akad. Nauk SSSR 235, 1347 (1977); C.A. 87, 200733 (1977). Unpublished data from the author's laboratory.
69. C. S. Subramaniam et al., Synthesis 1978, 468.
70. T. A. Hase, K. McCoy, Synth. Commun. 1979, 63.
71. H. Yatagai, Y. Yamamoto, K. Maruyama, J. Am. Chem. Soc. 102, 4548 (1980).
72. T. Takahashi et al., J. Am. chem. Soc. 101, 5072 (1979).
73. T. Kametani et al., Yakugaku Zasshi 100, 192 (1980); C.A. 93, 150202 (1980).
74. C. S. Subramaniam et al., J. Chem. Soc. Perkin Trans. I 1979, 2346, .
75. J. Tsuji, T. Mandai, Tetrahedron Lett. 1978, 1817.
76. T. Takahashi, K. Kasuga, J. Tsuji, Tetrahedron Lett. 1978, 4917.
77. J. Tsuji, M. Kailo, T. Takahashi, Bull. Chem. Soc. Jpn. 51, 547 (1978).
78. T. Takahashi, H. Ikeda, J. Tsuji, Tetrahedron Lett. 21, 3885 (1980).
79. T. Takahashi, I. Minami, I. Tsuji, Tetrahedron Lett. 22, 2651 (1981).
80. J. Tsuji, T. Yamakawa, T. Mandai, Tetrahedron Lett. 1979, 3741.
81. J. Tsuji et al., Bull. Chem. Soc. Jpn. 51, 1915 (1978).
82. J. Tsuji et al., Tetrahedron Lett. 1979, 2257.
83. J. Tsuji, M. Masaoka, T. Takahashi, Tetrahedron Lett. 1977, 2267.
84. J. Tsuji, H. Yasuda, Synth. Commun. 8, 103 (1978).
85. J. Yoshida et al., Tetrahedron Lett. 1978, 2161.
86. J. Tsuji et al., Chem. Lett. 1976, 773.
87. P.M. Henry, J. Am. Chem. Soc. 88, 1595 (1966).
88. P.M. Henry, J. Am. Chem. Soc. 94, 1527, 5200 (1972);.J. Chem. Soc. Chem. Commun. 1971, 328.
89. L.E. Overman, F.M. Knoll, Tetrahedron Lett. 1979, 321.
90. P. Boontanonda, R. Grigg, J. Chem. Soc. Chem. Commun 1977, 583.
91. J. Tsuji, Ann. N. Y. Acad. Sci. 333, 250 (1980).
92. J. Tsuji, Top. Current Chem. 91, 30 (1980), Springer-Verlag.
93. J. Tsuji, Pure Appl. Chem. 53, 2371 (1981).
94. J. Tsuji, T. Yamada, I. Shimizu, J. Org. Chem. 45, 5209 (1980).
95. K. Iseki et al., Tetrahedron 37, 4411 (1981).
96. E. Wenkert et al., J. Am. Chem. Soc. 100, 1267 (1978).
97. P.D. Magnus, M.S. Nobbs, Synth. Commun., 10, 273 (1980).
98. J. Tsuji, Y. Kobayashi, I. Shimizu, Tetrahedron Lett. 1979, 39.
99. M. Ochiai, M. Arimoto, E. Fujita, Tetrahedron Lett. 22. 1115 (1981).
100. F. Sato et al., Tetrahedron Lett. 24, 1041 (1983).
101. Hosomi, H. Kobayashi, H. Sakurai, Tetrahedron Lett. 21, 955 (1980).
102. T. Yanami, M. Miyashita, A. Yoshikoshi, J. Org. Chem. 45, 607 (1980).
103. M.A. Tius, A. Thurkauf, J. W, Truesdell, Tetrahedron Lett. 23, 2819 (1982).
104. J.E. McMurry, L.C. Blaszcak, J. Org. Chem. 39, 2217 (1974).
105. J. Tsuji et al., J. Am. Chem. Soc. 101, 5070 (1979).
106. N. Cohen, Acc. Chem., Res. 9, 412 (1976).
107. U. Eder et al. Chem. Ber. 108, 2673 (1975).
108. I. Shimizu, Y. Naito, .I. Tsuji, Tetrahedron Lett. 21, 487 (1980).
109. J. Tsuji, Y. Kobayashi, T. Takahashi, Tetrahedron Lett. 21. 483 (1980).
110. T. Takahashi. H. Yamada, J. Tsuji, J. Am. Chem. Soc. 103, 5259 (1981).
111. S. Kobayashi et al., Shokuhai 10, 24 (1968); C.A. 96. 76327 (1968).
112. J.E. Byrd et al. J. Chem. Soc. Chem. Commun. 1971, 40.
113. T. Sasaki, K. Kanematsu, A. Kondo, J. Chem. Soc. Trans. Per-kin 1. 1976, 2516.
114. J. Tsuji, S. Imamura, Bull. Chem. Soc. Jpn. 40, 197 (1967).
115. H. Nagashima, K. Sakai, J. Tsuji, Chem. Lett. 1982, 859.
116. S. Takano. Y. Imamura, K. Oga'sawara, Tetrahedron Lett. 22, 4479 (1981).
117. V.P. Kurkov, U.S. Patent 4031 115, Chevron Research Co, (1977); C.A. 87, 101966 (1977).
118. J. Tsuji, H. Nagashima, K. Hori, Tetrahedron Lett. 23, 2679 (1982).