Chinese Journal of Organic Chemistry >
Advances in the Synthesis of Organic Azides
Received date: 2012-06-24
Revised date: 2012-07-18
Online published: 2012-07-28
Supported by
Project supported by the National Natural Science Foundation of China (No. 21262020) and the Science and Technology Planning Project of Yunnan Province (No. KKSY201207047).
The recent advances in the synthesis of organic azides are reviewed, based on the categories of these compounds including alkyl azides, alkenyl azides, aryl azides and acyl azides. Mechanism of some reactions is also discussed.
Key words： organic azides; synthesis; advances
Jiang Yubo , Kuang Chunxiang , Han Chunmei , Wang Hong , Liang Xueqiua . Advances in the Synthesis of Organic Azides[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2231 -2238 . DOI: 10.6023/cjoc201206023
[1] Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
[2] (a) Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974.
(b) Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272.
[3] (a) Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620.
(b) Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338.
(c) Bohn, M. A.; Hammerl, A.; Harris, K.; Klapotke, T. M. Cent. Eur. J. Energ. Mater. 2005, 2, 3.
(d) Niu, X.; Zhang, J.; Wang, Y.; Chen. T.; Zhang, S.; Zhang, T.; Zhou, Z.; Yang, L. Acta Chim. Sinica 2011, 69, 610 (in Chinese).
(牛晓庆, 张建国, 王颖, 陈陶平, 张绍文, 张同来, 周遵宁, 杨利, 化学学报, 2011, 69, 610.)
[4] Griess, P. Liebigs Ann. Chem. 1866, 137, 39.
[5] (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
(b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
[6] (a) Maryam, C. H.; Roghayeh, C.; Maryam, B.; Ghaffar, H.; Hamed, T. Chin. J. Chem. 2012, 30, 223.
(b) Stengel, I.; Strassert, C. A.; Plummer, E. A.; Chien, C. H.; Cola, L.; Bäuerle, P. Eur. J. Inorg. Chem. 2012, 1795.
(c) Budin, I.; Devaraj, N. K. J. Am. Chem. Soc. 2012, 134, 751.
(d) Sohn, C. H.; Lee, J. E.; Sweredoski, M. J.; Graham, R. L. J.; Smith, G. T.; Hess, S.; Czerwieniec, G.; Loo, J. A.; Deshaies, R. J.; Beauchamp, J. L. J. Am. Chem. Soc. 2012, 134, 2672.
(e) Wei, J.; Chen, J.; Xu, J.; Cao, L.; Deng, H.; Sheng, W.; Zhang, H.; Cao, W. J. Fluorine Chem. 2012, 133, 146.
[7] Ciocoiu, C.; Nikolic, N.; Nguyen, H.; Thoresen, G. H.; Aasen, A. J.; Hansen, T. V. Eur. J. Med. Chem. 2010, 45, 3047.
[8] Zarei, A.; Hajipour, A. R.; Khazdooz, L.; Aghaei, H. Tetrahedron Lett. 2009, 50, 4443.
[9] Lowe-Ma, C.; Nissan, R.; Wilson, W. J. Org. Chem. 1990, 55, 3755.
[10] Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
[11] Tao, C.; Cui,X.; Li, J.; Liu, A.; Liu, L.; Guo, Q. Tetrahedron Lett. 2007, 48, 3525.
[12] Jin H.; Huang, Z. D.; Kuang, C. X.; Wang, X. K. Chin. Chem. Lett. 2011, 22, 310.
[13] Nair, V.; George, T. Tetrahedron Lett. 2000, 41, 3199.
[14] Hassner, A.; Levy, L. J. Am. Chem. Soc. 1965, 87, 4203.
[15] Brien, A.; Levesque, F.; Seeberger, P. Chem. Commun. 2011, 47, 2688.
[16] Yan, J.; Jin, H.; Chen, Z. J. Chem. Res. 2007, 233.
[17] Chakraborty, T.; Reddy, G. Tetrahedron Lett. 1990, 31, 1335.
[18] Boyer, J.; Hamer, J. J. Am. Chem. Soc. 1955, 77, 951.
[19] (a) Lobez, J.; Swager, T. Angew. Chem., In. Ed. 2010, 49, 95.
(b) Fuchs, M.; Goessler, W.; Pilger, C.; Kappe, C. Adv. Synth. Catal. 2010, 352, 323.
[20] Zheng, W.; Hsieh, Y.; Chiu, Y.; Cai, S.; Cheng, C.; Chen, C. J. Mater. Chem. 2009, 19, 8432.
[21] Ju, Y.; Kumar, D.; Varma, R. S. J. Org. Chem. 2006, 71, 6697.
[22] Zeng, H.; Tian, Q.; Shao, H. Green Chem. Lett. Rev. 2011, 4, 281.
[23] Viuf, C.; Bols, M. Angew. Chem., Int. Ed. 2001, 40, 623.
[24] Guerin, D.; Horstmann, T.; Miller, S. Org. Lett. 1999, 1, 1107.
[25] Suarez, J. R.; Trastoy, B.; Perez-Ojeda, M. E.; Marin-Barrios, R.; Chiara, J. L. Adv. Synth. Catal. 2010, 352, 2515.
[26] Katritzky, A. R.; Khatib, M. E.; Bol'shakov, O.; Khelashvili, L.; Steel, P. J. J. Org. Chem. 2010, 75, 6532.
[27] Hajipour, A. R.; Rajaei, A.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 708.
[28] Mukaiyama, T.; Kuroda, K.; Maruyama, Y.; Hayashi, Y. Chem. Lett. 2008, 37, 1072.
[29] Nettekoven, M. Synlett 2001, 1917.
[30] Ikeda, R.; Iwaki, T.; Iida,T.; Okabayashi, T.; Nishi, E.; Kurosawa, M.; Sakai, N.; Konakahara, T. Eur. J. Med. Chem. 2011, 46, 636.
[31] Kong, L.; Hu, J.; Zhang, L. J. Zhejiang Univ. (Nat. Sci.) 2010, 33, 185 (in Chinese).
(孔黎春, 胡洁玲, 孔龙峰, 浙江师范大学学报(自然科学版), 2010, 33, 185.)
[32] Zhong, Z.; Hu, J.; Wang, X.; Liu, J.; Zhang, L. Synth. Commun. 2011, 41, 2461.
[33] Rawal, V. H.; Zhong, H. M. Tetrahedron Lett. 1994, 35(28), 4947.
[34] Gao, Z.; Zhang, X. Chin. J. Inorg. Chem. 2002, 18, 683 (in Chinese).
(高占先, 张小航, 无机化学学报, 2002, 18, 683.)
[35] Padwa, A.; Crawford, K. R.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2003, 68, 2609.
[36] Swetha, M.; Ramana, P. V.; Shirodkar, S. G. Org. Prep. Proced. Int. 2011, 43, 348.
[37] Liu, W.; Tang, Y.; Guo, Y.; Sun, B.; Zhu, H.; Xiao, Y.; Dong, D.; Yang, C. Appl. Organomet. Chem. 2012, 26, 189.
[38] Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2002, 43, 1345.
[39] Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2002, 43, 3413.
[40] Kangani, C. O.; Day, B. W.; Kelley, D. E. Tetrahedron Lett. 2007, 48, 5933.
[41] Nowrouzi, N.; Jonaghani, M. Z. Chin. Chem. Lett. 2012, 23, 442.
[42] Bose, D. S.; Reddy, A. V. N. Tetrahedron Lett. 2003, 44, 3543.
[43] Marinescu, L.; Thinggaard, J.; Thomsen, I. B.; Bols, M. J. Org. Chem. 2003, 68, 9453.
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