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Application of Azodicarboxylates in Organic Synthesis

  • Xu Xiaoliang ,
  • Cheng Guohua ,
  • Li Xiaonian
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  • College of Chemical Engineering and Material Science, Zhejiang University of Technology, Hangzhou 310032

Received date: 2011-10-31

  Revised date: 2011-12-16

  Online published: 2011-01-06

Supported by

Project supported by the National Natural Science Foundation of China (No. 20872131).

Abstract

Azodicarboxylates, as versatile reagents, have been widely used in organic synthesis due to their unique electronic and structural properties. They have played important roles in organic synthesis such as Mitsunobu reaction, amination of carbonyl compounds and unsaturated hydrocarbons, synthesis of heterocyclic compounds. Besides these, azodicarboxylates can be used as oxidants for the dehydrogenation of alcohols and amines. Based on their previous applications, new progress of azodicarboxylates in synthetic chemistry in recent years is summarized and an outlook on their development is also given.

Cite this article

Xu Xiaoliang , Cheng Guohua , Li Xiaonian . Application of Azodicarboxylates in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1024 -1040 . DOI: 10.6023/cjoc1110313

References

[1] (a) Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc.Jpn. 1967, 40, 935.(b) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40,2380.(c) Mitsunobu, O.; Eguchi, M. Bull. Chem. Soc. Jpn. 1971, 44,3427.(d) Mitsunobu, O. Synthesis 1981, 1.
[2] (a) Dandapani, S.; Curran, D. P. Chem. Eur. J. 2004, 10, 3130.(b) Dembinski, R. Eur. J. Org. Chem. 2004, 2763.(c) But, T. Y. S.; Toy, P. H. Chem. Asian J. 2007, 2, 1340.
[3] (a) Huisgen, R.; Jakob, F. Justus Liebigs Ann. Chem. 1954, 590, 37.(b) Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986,108, 6394.(c) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am.Chem. Soc. 1986, 108, 6395.(d) Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108,6397.(e) Evans, D. A.; Nelson, S. G.. J. Am. Chem. Soc. 1997, 119, 6452.(f) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.(g) Yamashita, Y.; Ishitani, H.; Kobayashi, S. Can. J. Chem. 2000,78, 666.
[4] (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656.(b) B?gevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; J?rgensen,K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.(c) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; B?gevig, A.;J?rgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.(d) Liu, T. Y.; Cui, H. L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z. Q.;Chen, Y. C. Org. Lett. 2007, 9, 3671.(e) Hayashi, Y.; Aratake, S.; Imai, Y.; Hibino, K.; Chen, Q. Y.;Yamaguchi, J.; Uchimaru, T. Chem. Asian J. 2008, 3 225.(f) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003,2448.(g) Baumann, T.; Vogt, H.; Brase, S. Eur. J. Org. Chem. 2007, 266.(h) Baumann, T.; Bachle, M.; Hartmann, C.; Brase, S. Eur. J. Org.Chem. 2008, 2207.(i) Hartmann, C. E.; Baumann, T.; Bachle, M.; Brase, S. Tetrahedron:Asymmetry 2010, 21, 1341.(j) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. Org. Lett.2003, 5, 1685.(k) Chowdari, N. S.; Barbas, C. F. Org. Lett. 2005, 7, 867.(l) Suri, J. T.; Steiner, D. D.; Barbas, C. F. Org. Lett. 2005, 7, 3885.(m) Kotru z, P.; Alemayehu, S.; Toma, S.; Schmalz, H. G.; Adler, A.Eur. J. Org. Chem. 2005, 4904.  
[5] (a) Dahlin, N.; B?gevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004,346, 1101.(b) Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.;Kj?rsgaard, A.; J?rgensen, K. A. J. Am. Chem. Soc. 2005, 127,18296.(c) Ding, X.; Jiang, H. L.; Zhu, C. J.; Cheng, Y. X. TetrahedronLett. 2010, 51, 6105.(d) Liu, P. M.; Chang, C.; Reddy, R. J.; Ting, Y. F.; Kuan, H. H.;Chen, K. Eur. J. Org. Chem. 2010, 42.(e) Thomassigny, C.; Prim, D.; Greck, C. Tetrahedron Lett. 2006,47, 1117.(f) Gosiewska, S.; Soni, R.; Clarkson, G. J.; Wills, M. TetrahedronLett. 2010, 51, 4214.(g) Fu, J. Y.; Huang, Q. C.; Wang, Q. W.; Wang, L. X.; Xu, X. Y.Tetrahedron Lett. 2010, 51, 4870.(h) Fu, J. Y.; Xu, X. Y.; Li, Y. C.; Huang, Q. C.; Wang, L. X. Org.Biomol. Chem. 2010, 8, 4524.(i) Fu, J. Y.; Yang, Q. C.; Wang, Q. L.; Ming, J. N.; Wang, F. Y.; Xu,X. Y.; Wang, L. X. J. Org. Chem. 2011, 76, 4661.(j) Liu, C.; Zhu, Q.; Huang, K. W.; Lu, Y. X. Org. Lett. 2011, 13,2638.(k) Makino, K.; Kubota, S.; Hara, S.; Sakaguchi, M.; Hamajima, A.;Hamada, Y. Tetrahedron 2009, 65, 9468.(l) Iwamura, H.; Mathew, S. P.; Blackmond, D. G. J. Am. Chem.Soc. 2004, 126, 11770.(m) Blackmond, D. G.; Moran, A.; Hughes, M.; Armstrong, A. J.Am. Chem. Soc. 2010, 132, 7598.  
[6] (a) Lee, D.; Otte, R. D. J. Org. Chem. 2004, 69, 3569.(b) Kim, Y. J.; Lee, D. Org. Lett. 2004, 6, 4351.(c) Ni, B.; Zhang, Q. Y.; Garre, S.; Headley, A. D. Adv. Synth.Catal. 2009, 351, 875.  
[7] (a) Juhl, K.; J?rgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420.(b) Marigo, M.; Juhl, K.; J?rgensen, K. A. Angew. Chem., Int. Ed.2003, 42, 1367.(c) Bernardi, L.; Zhuang, W.; J?rgensen, K. A. J. Am. Chem. Soc.2005, 127, 5772.(d) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.;Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342.(e) Mashiko, T.; Kumagai, N.; Shibasaki, M. Org. Lett. 2008, 10,2725.(f) Mashiko, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc.2009, 131, 14990.(g) Comelles, J.; Pericas, A.; Moreno-Manas, M.; Vallribera, A.;Drudis-Sole, G.; Lledos, A.; Parella, T.; Roglans, A.; Garcla-Granda, S.; Roces-Fernandez, L. J. Org. Chem. 2007, 72, 2077.(h) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128,16044.(i) He, R. J.; Wang, X. S.; Hashimoto, T.; Maruoka, K. Angew.Chem., Int. Ed. 2008, 47, 9466.(j) Konishi, H.; Lam, T. Y.; Malerich, J. P.; Rawal, V. H. Org. Lett.2010, 12, 2028.(k) Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565.(l) Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.(m) Ghosh, S.; Nandakumar, M. V.; Krautscheid, H.; Schneider, C.Tetrahedron Lett. 2010, 51, 1860.  
[8] (a) Saaby, S.; Bella, M.; J?rgensen, K. A. J. Am. Chem. Soc. 2004,126, 8120.(b) Liu, X. F.; Li, H. M.; Deng, L. Org. Lett. 2005, 7, 167.(c) Liu, Y. J.; Melgar-Fernandez, R.; Juaristi, E. J. Org. Chem.2007, 72, 1522.(d) Hasegawa, Y.; Watanabe, M.; Gridnev, I. D.; Ikariya, T. J. Am.Chem. Soc. 2008, 130, 2158.  
[9] (a) Marigo, M.; Schulte, T.; Franzen, J.; J?rgensen, K. A. J. Am.Chem. Soc. 2005, 127, 15710.(b) Bertelsen, S.; Marigo, M.; Brandes, S.; Diner, P.; J?rgensen, K.A. J. Am. Chem. Soc. 2006, 128, 12973.(c) Galzerano, P.; Pesciaioli, F.; Mazzanti, A.; Bartoli, G.;Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7892.  
[10] (a) Jenner, G.; Papadopoulos, M. J. Org. Chem. 1986, 51, 585.(b) Poulsen, T. B.; Alemparte, C.; J?rgensen, K. A. J. Am. Chem.Soc. 2005, 127, 11614.(c) Leblanc, Y.; Zamboni, R.; Bernstein, M. A. J. Org. Chem. 1991,56, 1971.(d) Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58,5261.(e) Waser, J.; Carreira, E. M. J. Am. Chem. Soc. 2004, 125, 5676.(f) Waser, J.; Gonzalez-Gomez, J. C.; Nambu, H.; Huber, P.; Carreira,E. M. Org. Lett. 2005, 7, 4249.(g) Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45,7933.(h) Chang, L.; Kuang, Y. L.; Qin, B.; Zhou, X.; Liu, X. H.; Lin, L.L.; Feng, X. M. Org. Lett. 2010, 12, 2214.  
[11] (a) Cheng, L.; Liu, L.; Wang, D.; Chen, Y. J. Org. Lett. 2009, 11,3874.(b) Qian, Z. Q.; Zhou, F.; Du, T. P.; Wang, B. L.; Ding, M.; Zhao,X. L.; Zhou, J. Chem. Commun. 2009, 6753.(c) Bui, T.; Borregan, M.; Barbas, C. F. J. Org. Chem. 2009, 74,8935.(d) Bui, T.; Hernandez-Torres, G.; Milite, C.; Barbas, C. F. Org.Lett. 2011, 12, 5696.(e) Yang, Z. G.; Wang, Z.; Bai, S.; Shen, K.; Chen, D. H.; Liu, X.H.; Lin, L. L.; Feng, X. M. Chem. Eur. J. 2010, 16, 6632.(f) Mouri, S.; Chen, Z. H.; Mitsunuma, H.; Furutachi, M.;Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255.(g) Selvakumar, K.; Vaithiyanathan, V.; Shanmugam, P. Chem.Commun. 2010, 2826.  
[12] (a) Lee, C. K.; Kim, S. J.; Hahn, C. S. J. Org. Chem. 1980, 45,1692.(b) Lee, C. K.; Ahn, Y. M. J. Org. Chem. 1990, 55, 3957.(c) Zaltsgendler, I.; Leblanc, Y.; Bernstein, M. A. Tetrahedron Lett.1993, 34, 2441.(d) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682.(e) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268.(f) Brandes, S.; Bella, M.; Kj?rsgaard, A; J?rgensen, K. A. Angew.Chem. Int. Ed. 2006, 45, 1147.(g) Yu, W. Y.; Sit, W. N.; Lai, K. M.; Zhou, Z. Y.; Chan, A. S. C. J.Am. Chem. Soc. 2008, 130, 3304.  
[13] (a) Brunn, B. E.; Huisgen, R. Angew. Chem. Int. Ed. 1969, 8, 513.(b) Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978.(c) Liu, Y. X.; Xu, C. F.; Liu, L. Z. Synthesis 2003, 1335.(d) Otte, R. D.; Sakata, T.; Guzei, I. A.; Lee, D. Org. Lett. 2005, 7,495.(e) Nair, V.; Biju, A. T.; Abhilash, K. G.; Menon, R. S.; Suresh, E.Org. Lett. 2005, 7, 2121.(f) Nair, V.; Biju, A. T.; Vinod, A. U.; Suresh, E. Org. Lett. 2005, 7,5139.(g) Girard, M.; Murphy, P.; Tsou, N. N. Tetrahedron Lett. 2005, 46,2449.(h) Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Tetrahedron Lett.2007, 48, 9018.(i) Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8,2213.(j) Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem.Int. Ed. 2007, 46, 2070.(k) Moebs-Sanchez, S.; Bouhadir, G.; Saffon, N.; Maron, L.;Bourissou, D. Chem. Commun. 2008, 3435.(l) Morriso, D. C. J. Org. Chem. 1958, 23, 1072.  
[14] (a) Cohen, B. S. G.; Zand, R.; Steel, C. J. Am. Chem. Soc. 1961, 83,2895.(b) Gillis, B. T.; Beck, P. E. J. Org. Chem. 1962, 27, 1947.(c) Allred, E. L; Anderson, C. J. Org. Chem. 1967, 32, 1874.(d) Marullo, N. P.; Alford, J. A. J. Org. Chem. 1968, 33, 2368.(e) Lahousse, H.; Martens, H. J.; Toppet, S.; Hoornaert, G. J. J. Org.Chem. 1982, 47, 2001.(f) Pindur, U.; Kim, M. H.; Rogge, M.; Massa, W.; Molinier, M. J.Org. Chem. 1992, 57, 910.(g) Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Jimenez, J.L.; Palacios, J. C.; Sanchez, J. B. J. Org. Chem. 1999, 64, 6297.(h) Minami, T.; Chikugo, T.; Hanamoto, T. J. Org. Chem. 1986, 51,2210.(i) Monbaliu, J. C.; Tinant, B.; Peeters, D.; Marchand-Brynaert, J.Tetrahedron Lett. 2010, 51, 1052.(j) Fitzsimmons, B. J.; Leblanc, Y.; Rokach, J. J. Am. Chem. Soc.1987, 109, 285.(k) Fitzsimmons, B. J.; Leblanc, Y.; Chan, N.; Rokach, J. J. Am.Chem. Soc. 1988, 110, 5229.(l) Leblanc, Y.; Fitzsimmons, B. J.; Springer, J. P.; Rokach, J. J. Am.Chem. Soc. 1989, 111, 2995.  
[15] (a) Ma, S. M.; Jiao. N.; Zheng, Z. L.; Ma, Z. C.; Lu, Z.; Ye, L. W.;Deng, Y. Q.; Chen, G. F. Org. Lett. 2004, 6, 2193.(b) Yang, Q.; Jiang, X. F.; Ma, S. M. Chem. Eur. J. 2007, 13, 9310.(c) Cheng, X.; Ma, S. M. Angew. Chem. Int. Ed. 2008, 47, 4581.(d) Shu, W.; Yang, Q.; Jia, G. C.; Ma, S. M. Tetrahedron Lett. 2008,64, 11159.(e) Cheng, X.; Ma, S. M. Chem. Commun. 2009, 4263.(f) Cui, S. L.; Wang, J.; Wang, Y. G. Org. Lett. 2008, 10, 13.(g) Basavaiah, D.; Roy, S. Org. Lett. 2008, 10, 1819.  
[16] (a) Wang, M. Z.; Xu, H. W.; Liu, Y. G.; Wong, M. K.; Che, C. M.Adv. Synth. Catal. 2006, 348, 2391.(b) Saleem, R. S. Z.; Tepe, J. J. J. Org. Chem. 2010, 75, 4330.(c) Su, Y. H.; Jiang, Z.; Hong, D.; Lu, P.; Wang, Y. G.; Lin, X. F.Tetrahedron Lett. 2010, 66, 2427.(d) Monge, D.; Jensen, K. L.; Marin, I.; J?rgensen, K. A. Org. Lett.2011, 13, 328.(e) Hong, D.; Zhu, Y. X.; Lin, X. F.; Wang, Y. G. Tetrahedron 2011,67, 650.  
[17] (a) Achiwa, K.; Yamada, S. Tetrahedron Lett. 1974, 15, 1799.(b) Berlin, J. M.; Fu, G. C. Angew. Chem. Int. Ed. 2008, 47, 7048.(c) Huang, X. L.; Chen, X. Y.; Ye, S. J. Org. Chem. 2009, 74, 7585.(d) Wei, D. H.; Zhu, Y. Y.; Zhang, C.; Sun, D. Z.; Zhang, W. J.;Tang, M. S. J. Mol. Catal. A: Chem. 2011, 334, 108.(e) Allen, A. D.; Huang, W. W.; Moore, P. A.; Far, A. R.; Tidwell, T.T. J. Org. Chem. 2000, 65, 5676.  
[18] (a) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Am. Chem. Soc. 1966, 88,2328.(b) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Org. Chem. 1967, 32, 727.(c) Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett.2004, 45, 1409.(d) Cao, H. T.; Gree, R. Tetrahedron Lett. 2009, 50, 1493.  
[19] (a) Xu, X. L.; Li, X. N.; Ma, L.; Ye, N.; Weng, B. J. J. Am. Chem.Soc. 2008, 130, 14048.(b) Xu, X. L.; Li, X. N. Org. Lett. 2009, 11, 1027.  
[20] (a) Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Shahin, R. TetrahedronLett. 2010, 51, 3508.(b) Reddy, B. V. S.; Reddy, S. M. S.; Madan, C. Tetrahedron Lett.2011, 52, 1432.  
[21] (a) Guijarro, A.; Rieke, R. D. Angew. Chem. Int. Ed. 1998, 37,1679.(b) Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett.1998, 39, 9157.(c) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org.Chem. 1999, 64, 9189.(d) Takahashi, T.; Li, Y. Z.; Ito, T.; Xu, F.; Nakajima, K.; Liu, Y. H.J. Am. Chem. Soc. 2002, 124, 1144.(e) Mukaiyama, T.; Takahashi, K. Tetrahedron Lett. 1968, 9, 5907.(f) Hummel, G.; Hindsgaul, O. Angew. Chem., Int. Ed. 1999, 38,1782.(g) Uemura, T.; Chatani, N. J. Org. Chem. 2005, 70, 8631.(h) Kisseljova, K.; Tsubrik, O.; Sillard, R.; Maeorg, S.; Maeorg, U.Org. Lett. 2006, 8, 43.(i) Muniz, K.; Nieger, M. Angew. Chem. Int. Ed. 2006, 45, 2305.(j) Muniz, K.; Iglesias, A. Angew. Chem. Int. Ed. 2007, 46, 6350.  
[22] (a) Axen, R.; Chaykovsky, M.; Witkop, B. J. Org. Chem. 1967, 32,4117.(b) Clarke, R. L.; Gambino, A. J.; Heckeler, M. L. J. Org. Chem.1978, 43, 4589.(c) Wamhoff, H.; Schupp, W. J. Org. Chem. 1986, 51, 2787.(d) Ohno, M.; Ishizaki, K.; Eguchi, S. J. Org. Chem. 1988, 53,1285.(e) Rieber, N.; Alberts, J.; Lipsky, J. A.; Lemal, D. M. J. Am. Chem.Soc. 1969, 91, 5668.(f) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.;Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275.(g) Chen, Q. A.; Zeng, W.; Zhou, Y. G. Tetrahedron Lett. 2009, 50,6866.  
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