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Progress in Chemistry 2007, Vol. 19 Issue (0203): 303-312 Previous Articles   Next Articles

• Review •

Hypervalent Iodine Compounds in Organic Synthesis

Pan Zhenliang1,2;Shen Yongwen1;Liang Yongmin1**   

  1. 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,China;

    2. College of Science, Henan Agricultural University, Zhengzhou 450002, China

  • Received: Revised: Online: Published:
  • Contact: Liang Yongmin
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As a kind of mild , high selective and environment-friendly oxidation reagents, hypervalent iodine compounds have been widely applied in organic synthesis. In recent years, variety of hypervalent iodine compounds with new structure and new reactions and their applications massively emerged, which made their application extend from the traditional alcohol oxidation to the synthesis of some complex structure compounds. The recent progress of hypervalent iodine compounds in organic synthetic reactions, such as the oxidation, addition, substitution and rearrangement, is summarized via the common members of the hypervalent iodine compound family with references. Author's research focus which is mainly on the addition of ketones and the substitution reaction of alkenes with hypervalent iodine compound ortho-iodoxybenzoic acid are introduced.
Key words: hypervalent iodine compounds, organic synthesis, oxidation, addition, substitution, rearrangement

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[ 1 ] Zhdankin V V , Stang P J . Chem. Rev. , 2002 , 102 : 2523 —2584
[ 2 ] Wirth T. Angew. Chem. Int . Ed. , 2005 , 44 : 3656 —3665
[ 3 ] Moriarty R M. J . Org. Chem. , 2005 , 70 : 2893 —2903
[ 4 ] Tohma H , Kita Y. Adv. Synth. Catal . , 2004 , 346 : 111 —124
[ 5 ] Skulski L. Molecules , 2000 , 5 : 1331 —1371
[ 6 ] 梁永民(Liang Y M) , 陈保华(Chen B H) , 马永祥(Ma Y X) .合成化学(Chinese Journal of Synthetic Chemistry) , 2002 , 10(2) : 98 —105
[ 7 ] 雷自强(Lei Z Q) , 马恒昌(Ma H C) . 化学通报(Chemistry) ,2005 , 9 : 650 —658
[ 8 ] 苏熠东(Su Y D) , 郑云红(Zheng Y H) , 李援朝(Li Y C) . 化学试剂(Chemical Reagent) , 2005 , 27(12) : 719 —725
[ 9 ] 柳枫(Liu F) , 胡惟孝(Hu W X) , 刘学峰(Liu X F) . 浙江化工(Zhejiang Chemical Industry) , 2005 , 36(2) , 30 —35
[10] Frigerio M, Santagostino M. Tetrahedron Lett . , 1994 , 35 (43) :8019 —8022
[11] Frigerio M, Santagostino M, Sputore S. J . Org. Chem. , 1995 ,60 (22) : 7272 —7276
[12] Corey E J , Palani A. Tetrahedron Lett . , 1995 , 36 (20) : 3485 —3488
[13] Corey E J , Palani A. Tetrahedron Lett . , 1995 , 36 (44) : 7945 —7948
[14] Nicolaou K C , Zhong Y L , Baran P S. Angew. Chem. Int . Ed. ,2000 , 39 : 622 —625
[15] Shukla V G, Salgaonkar P D , Akamanchi K G. J . Org. Chem. ,2003 , 68 (13) : 5422 —5425
[16] Surendra K, Krishnaveni N S , Rao K R. J . Org. Chem. , 2003 ,68 : 9119 —9121
[17] Barluenga J , Lopez L A , Lober O , et al . Angew. Chem. Int .Ed. , 2001 , 40 : 3389 —3392
[18] Ochiai M, Nakanishi A , Suefuji T. Org. Lett . , 2000 , 2 (19) :2923 —2926
[19] Camacho M B , Clark A E , Liebrecht T A. J . Am. Chem. Soc. ,2000 , 122 : 5210 —5211
[20] Dauban P , Saniere L , Tarrade A. J . Am. Chem. Soc. , 2001 ,123 : 7707 —7708
[21] Wurz R P , Charette A B. Org. Lett . , 2003 , 5 : 2327 —2329
[22] Li J Y, Liang J L , Che C M, et al . Tetrahedron Letters , 2004 ,45 : 2685 —2688
[23] Correa A , Tellitu I , DomVnguez E , et al . J . Org. Chem. , 2006 ,71(9) : 3501 —3505
[24] Yu C , Hu L. Tetrahedron Lett . , 2001 , 42 : 5167 —5170
[25] Roels J , Metz P. Synlett , 2001 , 789 —790
[26] Tohma H , Maegawa T , Kita Y. Synlett , 2003 , 723 —725
[27] Nicolaou K C , Zhong Y L , Baran P S. J . Am. Chem. Soc. ,2000 , 122 : 7596 —7597
[28] Nicolaou K C , Montagnon T , Baran P S. J . Am. Chem. Soc. ,2002 , 124 : 2245 —2258
[29] Nicolaou K C , Baran P S , Zhong Y. J . Am. Chem. Soc. , 2001 ,123 : 3183 —3185
[30] Nicolaou KC , Zhong Y L , Baran P S. Angew. Chem. Int . Ed. ,2000 , 39 : 625 —628
[31] Nicolaou K C , Zhong Y L , Baran P S. J . Am. Chem. Soc. ,2002 , 124 : 2233 —2244
[32] Nicolaou K C , Casey J N M, Montagnon T. J . Am. Chem. Soc. ,2004 , 126 : 5192 —5201
[33] Nicolaou KC , Mathison CJ N. Angew. Chem. Int . Ed. , 2005 ,44 : 5992 —5997
[34] Bose D S , Reddy A V N. Tetrahedron Letters , 2003 , 44 : 3543 —3545
[35] Tohma H , Takizawa S , Kita Y. J . Org. Chem. , 1999 , 64 :3519 —3523
[36] Daly A M, Renehan M F , Gilheany D G. Org. Lett . , 2001 , 3 :663 —666
[37] Mu R Z , Liu Z Q , Liu Z L. Adv. Synth. Catal . , 2005 , 347 :1333 —1336
[38] Ficht S , Mulbaier M, Giannis A. Tetrahedron , 2001 , 57 :4863 —4866
[39] Sorg G, Mengel A. Angew. Chem. Int . Ed. , 2001 , 40 : 4395 —4397
[40] Qian W X, Jin E L , Bao W L. Angew. Chem. Int . Ed. , 2005 ,44 : 952 —955
[41] Yadav J S , Reddy B V S , Basak A K. Tetrahedron , 2004 , 60 :2131 —2135
[42] Das B , Holla H , Venkateswarlu K. Tetrahedron Letters , 2005 ,46 : 8895 —8897
[43] Tohma H , Takizawa S , Kita Y. Angew. Chem. Int . Ed. , 2000 ,39(7) : 1306 —1308
[44] Tohma H , Morioka H , Kita Y. Tetrahedron Letters , 2001 , 42 :6899 —6902
[45] Thottumkara A P , Vinod T K. Tetrahedron Letters , 2002 , 43 :569 —572
[46] Yusubov M S , Wirth T. Org. Lett . , 2005 , 7 : 519 —521
[47] Moorthy J N , Singhal N. Tetrahedron Letters , 2004 , 45 : 5419 —5424
[48] Yusubov M S , Drygunova L A , Zhdankinc V V. Synthesis , 2004 ,14 : 2289 —2292
[49] Kirsching A , Plumeier C , Rose L. J . Chem. Soc. , Chem.Commun. , 1998 , 33 —34
[50] Hashem A , Jung A , Ries M, et al . Synlett , 1998 , 195 —197
[51] Mico A D , Margarita R , Piancatelli G. Chem. Commun. , 1997 ,1237 —1238
[52] Bruno M, Margarita R , Piancatelli G. Tetrahedron Letters , 1998 ,39 : 3847 —3848
[53] Mico A D , Margarita R , Piancatelli G. Tetrahedron , 1997 , 53 :16877 —16882
[54] Margarita R , Mercanti C , Parlanti L , Piancatelli G. Eur. J . Org.Chem. , 2000 , 1865 —1870
[55] Tingoli M, Tiecco M, Testaferri L. Synth. Commun. , 1998 , 28 :1769 —1778
[56] Hirt U H , Spingler B , Wirth T. J . Org. Chem. , 1998 , 63 :7674 —7679
[57] Shi L , Kim Y J , Gin D Y. J . Am. Chem. Soc. , 2001 , 123 :6939 —6940
[58] Pan Z L , Liu X Y, Liang Y M. Synthesis , 2005 , 3 : 437 —441
[59] Barluenga J , Maro-Arias M, González2Bobes F. Chem. Eur. J . ,2004 , 10 : 1677 —1682
[60] Margarita R , Mercanti C , Parlanti L. Eur. J . Org. Chem. ,2000 , 1865 —1870
[61] Nicolaou K C , Zhong Y L , Baran P S. Angew. Chem. Int . Ed. ,2000 , 39 : 622 —625
[62] Nicolaou K C , Baran P S , Zhong Y L. J . Am. Chem. Soc. ,2002 , 124 : 2212 —2220
[63] Muraki T , Yokoyama M, Togo H. J . Org. Chem. , 2000 , 65 :4679 —4684
[64] Ochiai M, Nagao Y. J . Synth. Org. Chem. , 1986 , 44 : 660 —664
[65] Ochiai M. Rev. Heteroatom Chem. , 1989 , 2 : 92 —101
[66] Stang P J . Angew. Chem. Int . Ed. Engl . , 1992 , 31 : 274 —285
[67] Kitamura T , Fukuoka T , Fujiwara Y. Synlett , 1996 , 7 : 659 —660
[68] Williamson B L , Stang P J , Arif A M. J . Am. Chem. Soc. ,1993 , 115 : 2590 —2597
[69] Stang P J , Zhdankin V V. J . Am. Chem. Soc. , 1991 , 113 :4571 —4576
[70] Kotali E , Varvoglis A , Bozopoulos A. J . Chem. Soc , Perkin Trans. I , 1989 , 827 —832
[71] Stang P J , Murch P. Tetrahedron Lett . , 1997 , 38 : 8793 —8794
[72] Chen D W, Takai K, Ochiai M. Tetrahedron Lett . , 1997 , 38 :821 —824
[73] Jenkin N E , Ware R W, Atkinson R N. Synth. Commun. , 2000 ,30 : 947 —953
[74] Kita Y, Tohma H , Hatanaka K, Takada T. J . Am. Chem. Soc. ,1994 , 116 : 3684 —3691
[75] Hamamoto H , Anilkumar G, Kita Y. Chem. Eur. J . , 2002 , 8 :5377 —5383
[76] Ward R S , Hughes D D. Tetrahedron , 2001 , 57 : 5633 —5639
[77] Huang WJ , Singh O V , Lee S S. Helv. Chimi . Acta , 2004 , 87 :167 —174
[78] Arisawa M, Ramesh N G, Kita Y. J . Org. Chem. , 2001 , 66 :59 —65
[79] Tohma H , Morioka H , Kita Y. Tetrahedron , 2001 , 57 : 345 —352
[80] Tohma H , Iwata M, Kita Y. Tetrahedron Letters , 2002 , 43 :9241 —9244
[81] Barluenga J , González-Bobes F , González J M. Angew. Chem.Int . Ed. , 2002 , 41 : 2556 —2558
[82] Barluenga J , Campos-Gomez E , Rodriguez D. Angew. Chem.Int . Ed. , 2005 , 44 : 5851 —5854
[83] Giri R , Chen X, Yu J Q. Angew. Chem. Int . Ed. , 2005 , 44 :2112 —2115
[84] Kirsch S F. J . Org. Chem. , 2005 , 70 : 10210 —10212
[85] Pan Z L , Liu X Y, Liang Y M. Tetrahedron Lett . , 2004 , 45 :4101 —4104
[86] Lee J C , Park J Y, Yoon S Y. Tetrahedron Lett . , 2004 , 45 :191 —193
[87] Ueno M, Nabana T , Togo H. J . Org. Chem. , 2003 , 68 :6424 —6426
[88] Abe S , Sakuratani K, Togo H. Synlett , 2001 , 22 —24
[89] Hirt U H , Schuster M F H , Wirth T. Eur. J . Org. Chem. ,2001 , 1569 —1579
[90] Ueno M, Nabana T , Togo H. J . Org. Chem. , 2003 , 68 :6424 —6426
[91] Panunzi B , Rotiroti L , Tingoli M. Tetrahedron Lett . , 2003 , 44 :8753 —8756
[92] Lee J C , Kim S , Shin W C. Synth. Commun. , 2000 , 30 :4271 —4275
[93] Ochiai M, Sueda T. Tetrahedron Lett . , 2004 , 45 : 3557 —3559
[94] Hamamoto H , Hata K, Kita Y. Tetrahedron Lett . , 2004 , 45 :2293 —2295
[95] Ozanne-Beaudenon A , Quideau S. Angew. Chem. Int . Ed. ,2005 , 44 : 7065 —7069
[96] Quideau S , PouysUgu L , Avellan A V. Tetrahedron Letters ,2001 , 42 : 7393 —7396
[97] Kikugawa Y, Nagashima A , Sakamoto T. J . Org. Chem. , 2003 ,68 : 6739 —6744
[98] Correa A , Tellitu I , DomVnguez E. J . Org. Chem. , 2005 , 70 :2256 —2264
[99] Zhou T , Chen Z C. Heteroatom Chemistry , 2002 , 13 : 617 —619
[100] 夏敏(Xia M) , 陈振初(Chen Z C) . 合成化学(Chinese Journal of Synthetic Chemistry) , 2001 , 9(5) : 439 —441
[101] Benhida R , Blanchard P , Fourrey J L. Tetrahedron Letters ,1998 , 39 : 6849 —6852
[102] D’Auria M, Mauriello G. Tetrahedron Letters , 1995 , 36 :4883 —4884
[103] Dohi T , Morimoto K, Kita Y. Org. Lett . , 2005 , 7 : 537 —540
[104] Wirth T , Hirt U H. Tetrahedron : Asymmetry , 1997 , 8 : 23 —26
[105] Hirt U H , Schuster M F H , Wirth T. Eur. J . Org. Chem. ,2001 , 1569 —1579
[106] Ibrahim H , Kleinbeck F , Togni A. Helv. Chimi . Acta , 2004 ,87 : 605 —610
[107] Boye A C , Meyer D , Wirth T. Org. Lett . , 2003 , 5 : 2157 —2159
[108] Justik M W, Koser G F. Tetrahedron Letters , 2004 , 45 : 6159 —6163
[109] Feldman K S , Vidulova D B. Tetrahedron Letters , 2004 , 45 :5035 —5037
[110] Moriarty R M, Prakash O , Duncan M P. J . Chem. Res. Synop. ,1996 , 9 : 432 —433
[111] Shibuya M, Ito S , Iwabuchi Y. Org. Lett . , 2004 , 6 : 4303 —4306
[112] Chen J M, Huang X. Synthesis , 2004 , 15 : 2459 —2462
[113] Yadav J S , Reddy B V S , Reddy C S. Tetrahedron Lett . , 200445 : 4583 —4585
[114] Shukla V G, Salgaonkar P D , Akamanchi K G. Synlett , 2005 , 8 :1337 —1339
[115] Abo T , Sawaguchi M, Senboku H. Molecules , 2005 , 10 : 183 —189
[116] Varma R S , Kumar D. Synthesis , 1999 , 1288 —1290
[117] Mili Y, Fujita R , Matsushita K. J . Chem. Soc. Perkin Trans. 1 ,1998 , 2533 —2536
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