中文
Earlier issues
Announcement
More
Progress in Chemistry 2007, Vol. 19 Issue (11): 1727-1735 Previous Articles   Next Articles

• Review •

Nitroxyl Radical TEMPO: An Organocatalyst for Highly Efficient and Selective Oxidation of Alcohol

Yang Guanyu** ;Guo Yanchun; Wu Guanghui; Zheng Liwen; Song Maoping**   

  1. (Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China)
  • Received: Revised: Online: Published:
  • Contact: Yang Guanyu;Song Maoping
PDF ( 6074 ) Cited
Export

EndNote

Ris

BibTeX

The oxidation of alcohols to aldehydes or ketones is one of the fundamental transformations in organic synthesis. Since the Anelli’s protocol（TEMPO/NaBr/NaOCl）was discovered, the oxidation of alcohol using TEMPO (2,2,6,6-tetramethyl-piperidyl-1-oxyl) as an organocatalyst has become a important methodology under mild conditions due to its very high efficiency and selectivity, and is widely applied in both laboratory and industry. The recent researches on TEMPO-catalyzed oxidation of alcohol focused on two fields: the investigations of catalytic systems for the green oxidation of alcohol with molecular oxygen as the terminal oxidant, and TEMPO immobilizations in order to realize recovery and recycling of the catalysts. With emphasis on the above two fields, this paper has reviewed the development and recent progress of TEMPO-catalyzed oxidation of alcohol.
Key words: TEMPO, Catalyst, Alcohol, Oxidation reaction

CLC Number: 

[ 1 ] Zhan B Z, Thompson A. Tetrahedron , 2004 , 60 : 2917 —2935
[ 2 ] Ten Brink G J , Arends I W C E , Sheldon R A. Science , 2000 ,287 : 1636 —1639
[ 3 ] Guan B T, Xing D , Shi Z J , et al . J . Am. Chem. Soc. , 2005 ,127 : 18004 —18005
[ 4 ] Sheldon R A , Arends I W C E , Dijksman A. Catalysis Today ,2000 , 57 : 157 —166
[ 5 ] Mallat T, Baiker A. Chem. Rev. , 2004 , 104 : 3037 —3058
[ 6 ] Enache D I , Edwards J K, Hutchings GJ , et al . Science , 2006 ,311 : 362 —364
[ 7 ] Son Y C , Makwana V D , Suib S L , et al . Angew. Chem. Int .Ed. , 2001 , 40 : 4280 —4083
[ 8 ] Musawir M, Davey P N , Kozhevnikov I V , et al . Chem.Commun. , 2003 , 1414 —1415
[ 9 ] Krishnaveni N S , Surendra K, Rao K R. Adv. Synth. Catal . ,2004 , 346 : 346 —350
[10] Edegger K, Mang H , Kroutil W, et al , J . Mol . Catal . A:Chem. , 2006 , 251 : 66 —70
[11] Csjernyik G, *ll A H , Báckvall J E , et al . J . Org. Chem. ,2002 , 67 : 1657 —1662
[12] Adam W, Saha-Mê ller C R , Ganeshpure P A. Chem. Rev. ,2001 , 101 : 3499 —3548
[13] De Nooy A EJ , Besemer A C , van Bekkum H. Synthesis , 1996 ,1153 —1176
[14] Sheldon R A , Arends I W C E. Adv. Synth. Catal . , 2004 , 346 :1051 —1071
[15] Sheldon R A , Arends I W C E. J . Mol . Catal . A: Chem. ,2006 , 251 : 200 —214
[16] Sheldon R A , Arends I W C E , Brink GJ T. Acc. Chem. Res. ,2002 , 35 : 774 —781
[17] Calderon F. Synlett , 2006 , 657 —658
[18] Minisci F , Punta C , Recupero F. J . Mol . Catal . A: Chem. ,2006 , 251 : 129 —149
[19] Minisci F , Recupero F , Pedulli G F , et al . J . Mol . Catal . A:Chem. , 2003 , 204P205 : 63 —90
[20] Caron S , Dugger R W, Ripin D H B , et al . Chem. Rev. , 2006 ,106 : 2943 —2989
[21] Bjärsvik H R , Liguori L , Minisci F , et al . Org. Proc. Res.Dev. , 2002 , 6 : 197 —200
[22] Fritz-Langhals E. Org. Proc. Res. Develop. , 2005 , 9 : 577 —582
[23] Bragd P L , van Bekkum H , Besemer A C. Topics Catal . , 2004 ,27 : 49 —66
[24] Mahoney L R , Mendenhall G D , Ingold K U. J . Am. Chem.Soc. , 1973 , 95 : 8610 —8614
[25] Ganiev I M, Timerghazin Q K, Khalizov A F , et al . J . Phys.Org. Chem. , 2001 , 14 : 38 —42
[26] Minisci F , Recupero F , Cecchetto A , et al . Eur. J . Org.Chem. , 2004 , 109 —119
[27] Ma Z K, Bobbitt J M. J . Org. Chem. , 1991 , 56 : 6110 —6114
[28] Golubev V A , Rozantsev E G, Neiman M B. Bull . Acad. Sci .USSR , Chem. Ser. , 1965 , 14 : 1898
[29] Rychovsky S D , Vaidyanathan R. J . Org. Chem. , 1999 , 64 :310 —312
[30] Bolm C , Magnus A S , Hildebrand J P. Org. Lett . , 2000 , 2 :1173 —1175
[31] Hunter D H , Barton D H R , Motherwell WJ . Tetrahedron Lett . ,1984 , 25 : 603 —606
[32] Kim S S , Nehru K. Synlett , 2002 , 616 —618
[33] De Luca L , Giacomelli G, Masala S , Porcheddu A. J . Org.Chem. , 2003 , 68 : 4999 —5001
[34] De Luca L , Giacomelli G, Porcheddu A. Org. Lett . , 2001 , 3 :3041 —3043
[35] Semmelhack M F , Chou C S , Cortes D A. J . Am. Chem. Soc. ,1983 , 105 : 4492 —4494
[36] Palmisano G, Ciriminna R , Pagliaro M. Adv. Synth. Catal . ,2006 , 348 : 2033 —2037
[37] Anelli P L , Biffi C , Montanari F , Quici S. J . Org. Chem. ,1987 , 52 : 2559 —2562
[38] Anelli P L , Banfi S , Montanari F , Quici S. J . Org. Chem. ,1989 , 54 : 2970 —2972
[39] Anelli P L , Montanari F , Quici S. Org. Synth. , 1990 , 69 :212 —219
[40] Lin F , Peng W, Yu B , et al . Carbohydr. Res. , 2004 , 339 :1409 —1409
[41] Zhao M Z, Li J , Mano E , Reider P J , et al . J . Org. Chem. ,1999 , 64 : 2564 —2566
[42] Melvin F , McNeill A , Herbert R B , et al . Tetrahedron Lett . ,1999 , 40 : 1201 —1202
[43] Semmelhack M F , Schmid C R , Cortés D A , et al . J . Am.Chem. Soc. , 1984 , 106 : 3374 —3376
[44] Betzemeier B , Cavazzini M, Knochel P , et al . Tetrahedron Lett . ,2000 , 41 : 4343 —4346
[45] Ragagnin G, Betzemeier B , Knochel P , et al . Tetrahedron ,2002 , 58 : 3985 —3991
[46] Gamez P , Arends I W C E , Sheldon R A , et al . Chem.Commun. , 2003 , 2414 —2415
[47] Gamez P , Arends I W C E , Sheldon R A , et al . Adv. Synth.Catal . , 2004 , 346 : 805 —811
[48] Striegler S. Tetrahedron , 2006 , 62 : 9109 —9114
[49] Jiang N , Ragauskas A J . J . Org. Chem. , 2006 , 71 : 7087 —7090
[50] Jiang N , Ragauskas A J . Org. Lett . , 2005 , 7 : 3689 —3692
[51] Velusamy S , Srinivasan A , Punniyamurthy T. Tetrahedron Lett . ,2006 , 47 : 923 —926
[52] Boudreau J , Doucette M, Ajjou A N. Tetrahedron Lett . , 2006 ,47 : 1695 —1698
[53] Velusamy S , Punniyamurthy T. Eur. J . Org. Chem. , 2003 ,3913 —3915
[54] Cecchetto A , Fontana F , Miniscia F , et al . Tetrahedron Lett . ,2001 , 42 : 6651 —6653
[55] Dijksman A , Arends I W C E , Sheldon R A. Chem. Commun. ,1999 , 1591 —1592
[56] Dijksman A , Arends I W C E , Sheldon R A , et al . J . Am.Chem. Soc. , 2001 , 123 : 6826 —6833
[57] Kim S S , Jung H C. Synthesis , 2003 , 2135 —2137
[58] Wang N W, Liu R H , Liang X M, et al . Chem. Commun. ,2005 , 5322 —5324
[59] Yang G Y, Ma J P , Wang W, et al . Catal . Lett . , 2006 , 112 :83 —87
[60] Lenoir D. Angew. Chem. Int . Ed. , 2006 , 45 : 3206 —3210
[61] Liu R H , Liang X M, Hu X Q , et al . J . Am. Chem. Soc. ,2004 , 126 : 4112 —4113
[62] Liu R H , Liang X M, Hu X Q , et al . J . Org. Chem. , 2005 ,70 : 729 —731
[63] Xie Y, Mo W M, Hu X Q , et al . J . Org. Chem. , 2007 , 72 :4288 —4291
[64] Miller R A , Hoerrner R S. Org. Lett . , 2003 , 5 : 285 —287
[65] Lei M, Hu R J , Wang Y G. Tetrahedron , 2006 , 62 : 8928 —8932
[66] Vatele J M. Synlett , 2006 , 2055 —2058
[67] Schulze A , Giannis A. Synthesis , 2006 , 257 —260
[68] De Mico A , Margarita R , Piancatelli G, et al . J . Org. Chem. ,1997 , 62 : 6974 —6977
[69] Vatèle J M. Tetrahedron Lett . , 2006 , 47 : 715 —718
[70] Tashino Y, Togo H. Synlett , 2004 , 2010 —2012
[71] Sakuratani K, Togo H. Synthesis , 2003 , 21 —23
[72] Herrerías C I , Zhang T Y, Li CJ . Tetrahedron Lett . , 2006 , 47 :13 —17
[73] Fabbrini M, Galli C , Macchitella D , et al . Tetrahedron Lett . ,2001 , 42 : 7551 —7553
[74] Baiocco P , Barreca A M, Galli C , et al . Org. Biomol . Chem. ,2003 , 1 : 191 —197
[75] Galli C , Gentili P. J . Phys. Org. Chem. , 2004 , 17 : 973 —977
[76] Fabbrini M, Galli C , Gentili P J . Mol . Catal . B : Enz. , 2002 ,16 : 231 —240
[77] Arends I W C E , Li Y X, Sheldon R A , et al . Tetrahedron ,2006 , 62 : 6659 —6665
[78] Kulys J , Vidziunaite R. J . Mol . Catal . B : Enz. , 2005 , 37 :79 —83
[79] Ciriminna R , Bolm C , Pagliaro M, et al . Adv. Synth. Catal . ,2002 , 344 : 159 —163
[80] Bolm C , Fey T. Chem. Commun. , 1999 , 1795 —1796
[81] Testa M L , Ciriminna R , Pagliaro M, et al . Adv. Synth. Catal . ,2004 , 346 : 655 —660
[82] Ciriminna R , Pagliaro M. Adv. Synth. Catal . , 2003 , 345 :383 —388
[83] Ciriminna R , Blum J , Avnir D , Pagliaro M. Chem. Commun. ,2000 , 1441 —1442
[84] Brunel D , Fajula F , Nagy J B , et al . Appl . Catal . A: Gen. ,2001 , 213 : 73 —82
[85] Brunel D , Lentz P , Sutra P , et al . Stud. Surf . Sci . Catal . ,1999 , 125 : 237 —244
[86] Dijksman A , Arends I W C E , Sheldon R A. Chem. Commun. ,2000 , 271 —272
[87] Dijksman A , Arends I W C E , Sheldon R A. Synlett , 2001 ,102 —104
[88] Minisci F , Recupero F , Rodino M, et al . Org. Process Res.Dev. , 2003 , 7 : 794 —798
[89] Ferreira P , Hayes W, Tsang S C , et al . Green Chem. , 2004 , 6 :310 —312
[90] Benaglia M, Puglisi A , Pozzi G, et al . Tetrahedron , 2005 , 61 :　12058 —12064
[91] Pozzi G, Cavazzini M, Quici S , et al . Org. Lett . , 2004 , 6 :441 —443
[92] Cozzi F. Adv. Synth. Catal . , 2006 , 348 : 1367 —1390
[93] Gilhespy M, Lok M, Baucherel X. Catal . Today , 2006 , 117 :114 —119
[94] Gilhespy M, Lok M, Baucherel X. Chem. Commun. , 2005 ,1085 —1086
[95] Tanyeli C , Gümüä A. Tetrahedron Lett . , 2003 , 44 : 1639 —1642
[96] Kashiwagi Y, Ikezoe H , Ono T. Synlett , 2006 , 69 —72
[97] Wu X E , Ma L , Gao L X, et al . Synlett , 2005 , 607 —610
[98] Holczknecht O , Cavazzini M, Pozzi G, et al . Adv. Synth.Catal . , 2005 , 347 : 677 —688
[99] Pozzi G, Cavazzini M, Holczknecht O , et al . Tetrahedron Lett . ,2004 , 45 : 4249 —4251
[100] Gheorghe A , Cuevas2Yanez E , Reiser O , et al . Synlett , 2006 ,2767 —2770
[1] Jiaye Li, Peng Zhang, Yuan Pan. Single-Atom Catalysts for Electrocatalytic Carbon Dioxide Reduction at High Current Densities [J]. Progress in Chemistry, 2023, 35(4): 643-654.
[2] Yuewen Shao, Qingyang Li, Xinyi Dong, Mengjiao Fan, Lijun Zhang, Xun Hu. Heterogeneous Bifunctional Catalysts for Catalyzing Conversion of Levulinic Acid to γ-Valerolactone [J]. Progress in Chemistry, 2023, 35(4): 593-605.
[3] Yixue Xu, Shishi Li, Xiaoshuang Ma, Xiaojin Liu, Jianjun Ding, Yuqiao Wang. Surface/Interface Modulation Enhanced Photogenerated Carrier Separation and Transfer of Bismuth-Based Catalysts [J]. Progress in Chemistry, 2023, 35(4): 509-518.
[4] Yue Yang, Ke Xu, Xuelu Ma. Catalytic Mechanism of Oxygen Vacancy Defects in Metal Oxides [J]. Progress in Chemistry, 2023, 35(4): 543-559.
[5] Chunyi Ye, Yang Yang, Xuexian Wu, Ping Ding, Jingli Luo, Xianzhu Fu. Preparation and Application of Palladium-Copper Nano Electrocatalysts [J]. Progress in Chemistry, 2022, 34(9): 1896-1910.
[6] Zonghan Xue, Nan Ma, Weigang Wang. Nitrated Mono-Aromatic Hydrocarbons in the Atmosphere [J]. Progress in Chemistry, 2022, 34(9): 2094-2107.
[7] Leyi Wang, Niu Li. Relation Among Cu2+, Brønsted Acid Sites and Framework Al Distribution: NH3-SCR Performance of Cu-SSZ-13 Formed with Different Templates [J]. Progress in Chemistry, 2022, 34(8): 1688-1705.
[8] Qiyue Yang, Qiaomei Wu, Jiarong Qiu, Xianhai Zeng, Xing Tang, Liangqing Zhang. Catalytic Conversion of Bio-Based Platform Compounds to Fufuryl Alcohol [J]. Progress in Chemistry, 2022, 34(8): 1748-1759.
[9] Bin Jia, Xiaolei Liu, Zhiming Liu. Selective Catalytic Reduction of NOx by Hydrogen over Noble Metal Catalysts [J]. Progress in Chemistry, 2022, 34(8): 1678-1687.
[10] Mingjue Zhang, Changpo Fan, Long Wang, Xuejing Wu, Yu Zhou, Jun Wang. Catalytic Reaction Mechanism for Hydroxylation of Benzene to Phenol with H2O2/O2 as Oxidants [J]. Progress in Chemistry, 2022, 34(5): 1026-1041.
[11] Yaoyu Qiao, Xuehui Zhang, Xiaozhu Zhao, Chao Li, Naipu He. Preparation and Application of Graphene/Metal-Organic Frameworks Composites [J]. Progress in Chemistry, 2022, 34(5): 1181-1190.
[12] Yangyang Liu, Zigang Zhao, Hao Sun, Xianghui Meng, Guangjie Shao, Zhenbo Wang. Post-Treatment Technology Improves Fuel Cell Catalyst Stability [J]. Progress in Chemistry, 2022, 34(4): 973-982.
[13] Shujin Shen, Cheng Han, Bing Wang, Yingde Wang. Transition Metal Single-Atom Electrocatalysts for CO2 Reduction to CO [J]. Progress in Chemistry, 2022, 34(3): 533-546.
[14] 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.
[15] Yuanju Jing, Chun Kang, Yanxin Lin, Jie Gao, Xinbo Wang. MXene-Based Single-Atom Catalysts: Synthesis and Electrochemical Catalysis [J]. Progress in Chemistry, 2022, 34(11): 2373-2385.