中文
Announcement
More
Progress in Chemistry 2001, Vol. 13 Issue (06): 461- Previous Articles   Next Articles

• Review •

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

Li Huaming;Shu Huoming;Ye Xingkai;Wu Yue   

  1. Department of Chemistry, Hainan Normal University, Haikou 571158, China ; Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  • Received: Revised: Online: Published:
  • Contact: Li Huaming
PDF ( 2470 ) Cited
Export

EndNote

Ris

BibTeX

The development in the oxidation of olefins to ketones catalyzed by palladium compounds was reviewed. Some improved methods for the oxidation of olefins catalyzed by Wacker type catalyst systems are also summarized. For this reaction, some new catalyst systems and the reaction mechanism are escribed. Emphasis has been given to the applications of Pd(Ⅱ) HPA (heteropoly acid), Pd (Ⅱ) FePc (iron phthalocyanine) , Pd (Ⅱ) HQ (hydroquinone) FePc, Pd (Ⅱ) HQHPA , Pd (Ⅱ) CuSO4 HPA catalyst systems in the oxidation of olefins to ketones; the application of Pd (Ⅱ) LCoNO2, PdCl2 (MeCN )2 CuCl, Pd (OAc)2 pyridine, fluorous biphasic catalyst systems in the oxidation of olefins toketones is also surveyed.

CLC Number: 

[ 1 ] Jacobs P A. Handbook of Heterogeneous Catalysis Vol. 5 (eds.Ertl G, Knozinger H, Weitkamp J ). Weinheim: VCH, Verlag Gmb H, 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. 有机合成化学(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 (223) : 245—258
[ 7 ] Monflier E, Mortreux A , Aqueous-Phase Organometallic Catalysis (eds. Cornils B, Herrmann W A ). Weinheim: Wiley VCH, Verlag Gmb H, 1998. 513—518
[ 8 ] Henry P M. Palladium Catalyzed Oxidation of Hydrocarbons.Dordrecht, Holland: D. Reidel Publish ings Co, 1980
[ 9 ] Tsuji J. Palladium Reagents and Catalysts. Chichester: John Wiley and Sons, 1995
[ 10 ] Siegbahn P EM. 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 ] 金松寿(Jin S S). 有机催化(Organic Catalysis ). 上海(Shanghai ) : 上海科学技术出版社( Shanghai Science and Technology Press) , 1986. 220—229
[ 13 ] 奚祖威(Xi Z W ) , 杜文(Du W ) , 张铭俊(Zhang M J ). 均相催化进展(Advances in Homogeneous Catalysis) , 钱延龙, 廖世健主编(eds. Qian Y L , Liao S J ). 北京(Beijing) : 化学工业出版社( 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. , Perk in 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 IV , 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 ] 李华明(Li H M ) , 叶兴凯(Ye X K) , 吴越(Wu Y). 分子催化(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. 日本化学会志(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 H G, 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. CHEM TECH, 1992, 22 (8) : 498—501
[ 48 ] Arhancet J P, Davis M E, Hanson B E. Catal. Lett. , 1991,11: 129—136
[ 49 ] 林志彪(Lin Z B) , 叶品秋(Ye P Q ). 金属有机化学与催化(Organometallic Chemistry and Catalysis) , 钱延龙, 陈新滋主编(eds. Qian Y L , Cheng X Z). 北京(Beijing) : 化学工业出版社( 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, J anuszk iew icz K, A lper H. J. Mo l. 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. Mo l. Catal. A:Chem. , 2000, 157 (122) : 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 ] 胥勃(Xu B ) , 吴越(Wu Y). 化学通报(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 ] 卜部和夫, 木村文彦, 泉有亮. 触媒(Shokubai) , 1980, 22(1) : 10—12
[ 70 ] Urabe K, Kimura F, Izumi Y. in Proceedings of International Congress on Catalysis, Tokyo, J apan, 1980. 1478—1479
[ 71 ] 石井康敬. 触媒(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 ] 李华明(Li H M ) , 叶兴凯(Ye X K) , 吴越(Wu Y). 分子催化(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 ] 李华明(Li H M ) , 叶兴凯(Ye X K) , 吴越(Wu Y). 应用化学( Chin. J. Appl. Chem. ) , 1995, 12 (5) : 15—19
[ 80 ] 李华明(Li H M ) , 叶兴凯(Ye X K) , 吴越(Wu Y). 应用化学( Chin. J. Appl. Chem. ) , 1995, 12 (5) : 20—24
[ 81 ] 李华明(Li H M ) , 叶兴凯(Ye X K) , 吴越(Wu Y). 分子催化( J. Mol. Catal . Ch ina) , 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 ] 李华明(Li H M ). 硕士学位论文(M. S. Dissertation). 中国科学院长春应用化学研究所(Changchun Institute of Applied Chemistry, Chinese Academy of Sciences) , 1992
[ 85 ] Kim Y, Kim H, Lee J , Sim K, Han Y, Pai K 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. 化学工业(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 ] 叶兴凯(Ye X K) , 吴越(Wu Y) , Ercolani C. 分子催化(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. Mo l. 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. Mo l. 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. 有机合成化学(J. Synth. Org.Chem. Jpn. ) , 1995, 53 (11) : 1009—1020
[ 102 ] Nishimura T, Kakiuchi N , Onoue T, Ohe K, Uemura S. J.Chem. Soc. Perk in 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

[1] Bowen Xia, Bin Zhu, Jing Liu, Chunlin Chen, Jian Zhang. Synthesis of 2,5-Furandicarboxylic Acid by the Electrocatalytic Oxidation [J]. Progress in Chemistry, 2022, 34(8): 1661-1677.
[2] Xinglong Li, Yao Fu. Preparation of Furoic Acid by Oxidation of Furfural [J]. Progress in Chemistry, 2022, 34(6): 1263-1274.
[3] Peng Wang, Huan Liu, Da Yang. Recent Advances on Tandem Hydroformylation of Olefins [J]. Progress in Chemistry, 2022, 34(5): 1076-1087.
[4] Fei Wu, Wei Ren, Cheng Cheng, Yan Wang, Heng Lin, Hui Zhang. Biochar-Based Advanced Oxidation Processes for the Degradation of Organic Contaminants in Water [J]. Progress in Chemistry, 2022, 34(4): 992-1010.
[5] Hongyu Chu, Tianyu Wang, Chong-Chen Wang. Advanced Oxidation Processes (AOPs) for Bacteria Removal over MOFs-Based Materials [J]. Progress in Chemistry, 2022, 34(12): 2700-2714.
[6] Nan Wang, Yuqi Zhou, Ziye Jiang, Tianyu Lv, Jin Lin, Zhou Song, Lihua Zhu. Synergistically Consecutive Reduction and Oxidation of Per- and Poly-Halogenated Organic Pollutants [J]. Progress in Chemistry, 2022, 34(12): 2667-2685.
[7] Yuan Su, Keming Ji, Jiayao Xun, Liang Zhao, Kan Zhang, Ping Liu. Catalysts for Catalytic Oxidation of Formaldehyde and Reaction Mechanism [J]. Progress in Chemistry, 2021, 33(9): 1560-1570.
[8] Ming Ge, Zheng Hu, Quanbao He. Application of Spinel Ferrite-Based Advanced Oxidation Processes in Organic Wastewater Treatment [J]. Progress in Chemistry, 2021, 33(9): 1648-1664.
[9] Jia Liu, Jun Shi, Kun Fu, Chao Ding, Sicheng Gong, Huiping Deng. Heterogeneous Catalytic Persulfate Oxidation of Organic Pollutants in the Aquatic Environment: Nonradical Mechanism [J]. Progress in Chemistry, 2021, 33(8): 1311-1322.
[10] Wenliang Han, Linyang Dong. Activation Methods of Advanced Oxidation Processes Based on Sulfate Radical and Their Applications in The Degradation of Organic Pollutants [J]. Progress in Chemistry, 2021, 33(8): 1426-1439.
[11] Huan Song, Qi Zou, Keding Lu. Parameterization and Application of Hydroperoxyl Radicals(HO2) Heterogeneous Uptake Coefficient [J]. Progress in Chemistry, 2021, 33(7): 1175-1187.
[12] Xiaohong Yi, Chongchen Wang. Elimination of Emerging Organic Contaminants in Wastewater by Advanced Oxidation Process Over Iron-Based MOFs and Their Composites [J]. Progress in Chemistry, 2021, 33(3): 471-489.
[13] Lili Cheng, Yun Zhang, Yekun Zhu, Ying Wu. Selective Oxidation of HMF [J]. Progress in Chemistry, 2021, 33(2): 318-330.
[14] Xiaojing Li, Yonghong Li, Fuhang Yu, Weiyan Qi, Ye Jiang, Qianwen Lu. Catalysts for Removal of Xylene by Catalytic Oxidation [J]. Progress in Chemistry, 2021, 33(12): 2203-2214.
[15] Yong Feng, Yu Li, Guangguo Ying. Micro-Interface Electron Transfer Oxidation Based on Persulfate Activation [J]. Progress in Chemistry, 2021, 33(11): 2138-2149.