The Development in Oxidation of Olefins to Ketones Catalyzed by Palladium Compounds

Progress in Chemistry

Volumn 13, Issue 6, 2001, Pages 461-471

  Li, Huaming ^a   Shu, Huoming ^a   Ye, Xingkai ^b   Wu, Yue ^b  

^a HAINAN NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

Ketones; Olefin; Oxidation; Palladium compounds

Indexed keywords

EID: 0011464073     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (104)

1. Jacobs P A. Handbook of Heterogeneous Catalysis Vol. 5 (eds. Ertl G, Knozinger H, Weitkamp J). Weinheim: VCH, Verlag-GmbH, 1997. 2284-2295
2. Smidt J, Hafner W, Jira R, Sedlmeier J, Sieber R, Ruttinger R, Kojer H. Angew. Chem., 1959, 71(5): 176-182
3. Tsuji J. Synthesis, 1984, (5): 369-384
4. Tsuji J, Nokami J, Mandai T. (J. Synth. Org. Chem. Jpn.), 1989, 47(7): 649-659
5. Dedieu A. Catal. Met. Complexes, 1995, 18: 167-195
6. Lyons J E. Catal. Today, 1988, 3(2-3): 245-258
7. Monflier E, Mortreux A, Aqueous-Phase Organometallic Catalysis (eds. Cornils B, Herrmann W A). Weinheim: Wiley-VCH, Verlag GmbH, 1998. 513-518
8. Henry P M. Palladium Catalyzed Oxidation of Hydrocarbons. Dordrecht, Holland: D. Reidel Publishings Co, 1980
9. Tsuji J. Palladium Reagents and Catalysts. Chichester: John Wiley and Sons, 1995
10. Siegbahn P E M. J. Phys. Chem., 1996, 100(35): 14672-14680
11. Lyons J E. Oxygen Complexes and Oxygen Activation by Transition Metals (eds. Martell A E, Sawyer D T). New York and London: Plenum Press, 1988. 233-251
12. (Jin S S). (Organic Catalysis). (Shanghai ): (Shanghai Science and Technology Press), 1986. 220-229
13. (Xi Z W), (Du W), (Zhang M J). (Advances in Homogeneous Catalysis), (eds. Qian Y L, Liao S J). (Beijing): (Chemical Industry Press), 1990. 189-232
14. Clement W H, Selwitz C M. J. Org. Chem., 1964, 29(1): 241-243
15. Fahey D R, Zuech E A. J. Org. Chem., 1974, 39(22): 3276-3277
16. Lloyd W G, Luberoff B J. J. Org. Chem., 1969, 34(12): 3949-3952
17. Miller D G, Wayner D D M. J. Org. Chem., 1990, 55(9): 2924-2927
18. McQuillin F J, Parker D G. J. Chem. Soc., Perkin Trans. 1, 1974, (7): 809-815
19. Jira R, Freiesleben W. Organometal. React., 1972, 3: 1
20. Shitova N B, Kuznetsova L I, Matveev K I. Kinet. Katal., 1974, 15(1): 72-75
21. Mimoum H, Charpentier R, Mitschler A, Fischer J, Weiss R. J. Am. Chem. Soc., 1980, 102(3): 1047-1054
22. Kozhevnikov I V, Matveev K I. Appl. Catal., 1983, 5(2): 135-150
23. Matveev K I, Zhizhina E G, Shitova N B, Kuznetsova L I. Kinet. Katal., 1977, 18(2): 380-386
24. Davison S F, Mann B E, Maitlis P M. J. Chem. Soc. Dalton Trans., 1984, (6): 1223-1228
25. Ogawa H, Fujinami H, Taya K, Teratani S. Bull. Chem. Soc. Jpn., 1984, 57, (7): 1908-1913
26. Roussel M, Mimoum H. J. Org. Chem., 1980, 45(26): 5387-5390
27. (Li H M), (Ye X K), (Wu Y). (J. Mol. Catal. China), 1997, 11(4): 253-257
28. Heck R F. J. Am. Chem. Soc., 1968, 90(20): 5518-5526
29. Espeel P H, Tielen M C, Jacobs P A. J. Chem. Soc. Chem. Commun., 1991, (10): 669-671
30. Espeel P H, De Peuter G, Tielen M C, Jacobs P A. J. Phys. Chem., 1994, 98(44): 11588-11596
31. Fujimoto K, Takeda H, Kunugi T. Ind. Eng. Chem. Prod. Res. Develop., 1974, 13(4): 237-242
32. van der Haider E, Ammerlaan J A M, Gerritsen A W, Scholten J J F. J. Mol. Catal., 1989, 55: 320
33. Stobbe-Kreemers A W, Soede M, Makkee M, Scholten J J F. Appl. Catal. A: Gen., 1995, 131(2): 367-381
34. Stobbe-Kreemers A W, van der Zon M, Makkee M, Scholten J J F. J. Mol. Catal. A: Chem., 1996, 107: 247-253
35. Stobbe-Kreemers A W, Dielis R B, Makkee M, Scholten J J F. J. Catal., 1995, 154(2): 175-186
36. Stobbe-Kreemers A W, van der Lans G, Makkee M, Scholten J J F. J. Catal., 1995, 154(2): 187-193
37. Nowinska K, Dudko D, Golon R. Chem. Commun., 1996, (2): 277-279
38. Nowinska K, Sopa M, Dudko D, Mocna M. Catal. Lett., 1997, 49(1-2): 43-48
39. Soeda H, Okuhara T, Misono M. (Nippon Kagaku Kaishi), 1993, (8): 917-923
40. Kishi A, Higashino T, Sakaguchi S, Ishii Y. Tetrahedron Lett., 2000, 41(1): 99-102
41. Tang HG, Sherrington D C. Polymer, 1993, 34(13), 2821-2829
42. Tang H G, Sherrington D C. J. Catal., 1993, 142(2): 540-551
43. Tang H G, Sherrington D C. J. Mol. Catal., 1994, 94: 7-17
44. Jia C G, Jin F Y, Pan H Q, Huang M Y, Jiang Y Y. Macromol. Chem. Phys., 1994, 195: 751-758
45. Ahn J H, Sherrington D C. Macromolecules, 1996, 29(11): 4164-4165
46. Arhancet J P, Davis M E, Merola J S, Hanson B E. Nature, 1990, 339: 454-455
47. Davis M E. CHEMTECH, 1992, 22(8): 498-501
48. Arhancet J P, Davis M E, Hanson B E. Catal. Lett., 1991, 11: 129-136
49. (Lin Z B), (Ye P Q). (Organometallic Chemistry and Catalysis), (eds. Qian Y L, Cheng X Z). (Beijing): ( Chemical Industry Press), 1997. 519-536
50. Januszkiewicz K, Alper H. Tetrahedron Lett., 1983, 24 (47): 5159-5162
51. Alper H, Januszkiewicz K, Smith D J H. Tetrahedron Lett., 1985, 26(19): 2263-2264
52. Harada A, Hu Y, Takahashi S. Chem. Lett., 1986, (12): 2083-2084
53. Zahalka H, Januszkiewicz K, Alper H. J. Mol. Catal., 1986, 35(2): 249-253
54. Monflier E, Blouet E, Barbaux Y, Mortreux A. Angew. Chem. Int. Ed. Engl., 1994, 33(20): 2100-2102
55. Monflier E, Tilloy S, Fremy G, Barbaux Y, Mortreux A. Tetrahedron Lett., 1995, 36(3): 387-388
56. Monflier E, Tilloy S, Blouet E, Barbaux Y, Mortreux A. J. Mol. Catal. A: Chem., 1996, 109: 27-35
57. Mathias L J, Vaidya R A. J. Am. Chem. Soc., 1986, 108 (5): 1093-1094
58. Harada A. J. Synth. Org. Chem. Jpn., 1990, 48(6): 517-521
59. Tilloy S, Bertoux F, Mortreux A, Monflier E. Catal. Today, 1999, 48(1-4): 245-253
60. Karakhanov E, Maximov A, Kirillov A. J. Mol. Catal. A: Chem., 2000, 157(1-2): 25-30H
61. Ito H, Kasukawa T, Fujita M. Chem. Lett., 2000, (6): 598-599
62. Schwartz J, McMillan J W, Fischer H E. J. Mol. Catal., 1992, 74(3): 443-450
63. Nishinaga A, Yamada T, Fujisaw H, Ishizaki K, Ihara H, Matsuura T. J. Mol. Catal., 1988, 48(2-3): 249-264
64. Grate J H, Hamm D R, Mahajan S. Catalysis of Organic Reactions (eds. Kosak J R, Johnson T A), New York. Marcel Dekker, 1993. 213-264
65. (Xu B), (Wu Y). (Chemistry Bull.), 1985, (4): 34-40
66. Matveev K I, Shitova N B, Pai Z P, Odyakov V F, Akmalova O K, Ulrich M H, Kuznetsova L I, Basalaeva T A, Rumyantsev A V, Shadrin L P, Dzalalova M M. BP 1 508 331, 1978 (Chem. Abstr., 1979, 38531v)
67. Cihova M, Hrusovsky M, Voitko J, Matveev K I. React. Kinet. Catal. Lett., 1981, 16(4): 383-386
68. Ali B E, Bregeault J M, Martin J. J. Organometal. Chem., 1987, 327(1): C9-C14
69. (Shokubai), 1980, 22 (1), 10-12
70. Urabe K, Kimura F, Izumi Y. in Proceedings of VI International Congress on Catalysis, Tokyo, Japan, 1980. 1478-1479
71. (Shokubai), 1997, 39(1): 2-8
72. Kozhevnikov I V. Chem. Rev., 1998, 98(1): 171-198
73. Kozhevnikov I V. Catal. Rev. -Sci. Eng., 1995, 37(2): 311-352
74. (Li H M), (Ye X K), (Wu Y), (J. Mol. Catal. China), 1997, 11(5): 263-268
75. Backvall J E, Awasthi A K, Renko Z D. J. Am. Chem. Soc., 1987, 109(15): 4750-4752
76. Backvall J E, Hopkins R B. Tetrahedron Lett., 1988, 29 (23): 2885-2889
77. Backvall J E, Hopkins R B, Grennberg H, Mader M M, Awashi A K. J. Am. Chem. Soc., 1990, 112(13): 5160-5166
78. Li H M, Ye S K, Yang X G, Wu Y. Chin. J. Chem., 1997, 15(6): 512-527
79. (Li H M), (Ye X K), (Wu Y). (Chin. J. Appl. Chem.), 1995, 12(5): 15-19
80. (Li H M), (Ye X K), (Wu Y). (Chin. J. Appl. Chem.), 1995, 12(5): 20-24
81. (Li H M), (Ye X K), (Wu Y). (J. Mol. Catal. China), 1997, 11(4): 258-262
82. Setoyama T, Maki T. JP 05 140 020, 1993 (Chem. Abstr., 1993, 119, 225620c)
83. Srinivasan S, Ford W T. J. Mol. Catal., 1991, 64(3): 291-303
84. (Li H M). (M. S. Dissertation). (Changchun Institute of Applied Chemistry, Chinese Academy of Sciences), 1992
85. Kim Y, Kim H, Lee J, Sim K, Han Y, PaiK H. Appl. Catal. A: Gen., 1997, 155(1): 15-26
86. Yokta T, Fujibayashi S, Nishiyama Y, Sakaguchi S, Ishii Y. J. Mol. Catal. A: Chem., 1996, 114(1-3): 113-122
87. Horowitz H H. J. Appl. Electrochem., 1984, 14(6): 779-790
88. Inokuchi T, Izawa M. (Chemistry Industry), 1994, (2): 34-37
89. Tsuji J, Minato M. Tetrahedron Lett., 1987, 28 (32): 3683-3686
90. Miller D G, Wayner D D M. Can. J. Chem., 1992, 70(9): 2485-2490
91. Solar J P, Mares F, Diamond S E. Catal. Rev. -Sci. Eng., 1985, 27(1): 1-28
92. Tovrog B S, Mares F, Diamond S E. J. Am. Chem. Soc., 1980, 102(21): 6616-6618
93. (Ye X K), (Wu Y), Ercolani C. (J. Mol. Catal. China), 1989, 3(4): 292
94. Andrews M A, Kelly K P. J. Am. Chem. Soc., 1981, 103 (10): 2894-2896
95. Takehira K, Orita H, Oh I H, Leobardo C O, Martinez G C, Shimidzu M, Hayakawa T, Ishikawa T. J. Mol. Catal., 1987, 42(2): 247-255
96. Takehira K, Hayakawa T, Orita H, Shimizu M. J. Mol. Catal., 1989, 53(1): 15-21
97. Takehira K, Oh I H, Martinez V C, Chavira R S, Hayakawa T, Orita H, Shimidzu M, Ishikawa T. J. Mol. Catal., 1987, 42(2): 237-246
98. Jiang H F, Jia L Q, Li J H. Green Chem., 2000, 2: 161-164
99. Hosokawa T, Ataka Y, Murahashi S I. Bull. Chem. Soc. Jpn., 1990, 63(1): 166-169
100. Hosokawa T, Nakahira T, Takano M, Murahashi S I. J. Mol. Catal., 1992, 74: 489
101. Hosokawa T, Murahashi S I. (J. Synth. Org. Chem. Jpn.), 1995, 53(11): 1009-1020
102. Nishimura T, Kakiuchi N, Onoue T, Ohe K, Uemura S. J. Chem. Soc. Perkin Trans. 1, 2000, (12): 1915-1918
103. Horvath I T, Rabai J. Science, 1994, 266: 72-75
104. Betzemeier B, Lhermitte F, Knochel P. Tetrahedron Lett., 1998, 39(37): 6667-6670