Chinese Journal of Organic Chemistry >
Catalyst-Free Cyclopropanation of Alkenes with Diazocompounds under Microwave Irradiation
Received date: 2013-07-19
Revised date: 2013-08-19
Online published: 2013-08-29
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21074097, 21274112), and the Found of Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Educatio (No. JDGD-2012-07).
Cyclopropane derivatives were prepared by the reaction of diazocompounds and alkene without catalyst under microwave irradiation, which demonstrated that it is an efficient method in organic chemistry. Compared with traditional metal catalyzed cyclopropane, this method is convenient and less harmful to environment. A second-order process was involved in the cyclopropanation as shown by the kinetic study.
Key words: cyclopropanation; diazocompound; microwave; kinetic study; green chemistry
Cai Shaojun , Xiao Longqiang , Liao Liqiong , Liu Lijian . Catalyst-Free Cyclopropanation of Alkenes with Diazocompounds under Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2602 -2606 . DOI: 10.6023/cjoc201307030
[1] (a) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
(b) Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
(c) Xu, M.; Lin, G. Chin. J. Org. Chem. 2000, 20, 475.
(d) Zhu, L. Chin. J. Org. Chem. 1991, 11, 437.
(e) Yan, G.; Kuang, C.; Peng, C.; Wang, J. Chin. J. Org. Chem. 2009, 29, 813.
(f) Han, X.; Ye, L.; Sun, X. Chin. J. Org. Chem., 2009, 29, 309.
[2] (a) Thommes, K.; Kiefer, G.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2009, 48, 8115.
(b) Concellon, J. M.; Solla, H. R.; Concellon, C.; Amo, V. D. Chem. Soc. Rev. 2010, 39, 4103.
(c) Fields, K. B.; Engle, J. T.; Spripothongnak, S.; Kim, C.; Zhang, X. P.; Ziegler, C. J. Chem. Commun. 2011, 47, 749.
(d) Lyons, T. W.; Sanford, M. S. Tetrahedron 2009, 65, 3211.
(e) Zhou, Y.; Trewyn, B. G.; Angelici, R. J.; Woo, L. K. J. Am. Chem. Soc. 2009, 131, 11734.
(f) Lopez, J. G.; Rodriguea, V. Y.; Roces, L.; Granda, S. G.; Martinez, A.; Garcia, A. G.; Castro, G. R.; Villacorta, F. J.; Iglesias, M. J.; Ortiz, F. L. J. Am. Chem. Soc. 2010, 132, 10665.
(g) Illa, O.; Garcia, C. R.; Silva, C. A.; Favier, I.; Picurelli, D.; Oliva, A.; Gomez, M.; Branchadell, V.; Ortuno, R. M. Organometallics 2007, 26, 3306.
(h) Lindsay, V. N. G.; Icolas, C.; Charette, A. B. J. Am. Chem. Soc. 2011, 133, 8972.
(i) Wang, S. R.; Zhu, C. Y.; Sun, X. L.; Tang, Y. J. Am. Chem. Soc. 2009, 131, 4192.
(j) Moebius, D. C.; Kingsbury, J. S. J. Am. Chem. Soc. 2009, 131, 878.
(k) Suematsu, H.; Kanchiku, S.; Uchida, T.; Katsuki, T. J. Am. Chem. Soc. 2008, 130, 10327.
[3] (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
(b) Nadagouda, M. N.; Speth, T. F.; Varma, R. S. Acc. Chem. Res. 2011, 44, 469.
(c) Zhang, C.; Li, J.; Luo, Y.; Ge, Z. Acta Chim. Sinica 2012, 70, 492.
(d) Wang, Y.; Liu, Y.; Ruan, R.; Wan, Y.; Zhang, J.; Peng, H. Acta Chim. Sinica 2012, 70, 114.
(e) Wang, X.; Han, Y.; Yu, J.; Xu, R. Acta Chim. Sinica 2012, 70, 1496.
[4] (a) Ortiz, A. D.; Langa, F.; Hozand, A.; Moreno, A. Eur. J. Org. Chem. 2000, 4, 3659.
(b) Langa, F.; Cruz, P.; Espildora, E.; Garcia, J. J.; Perez, M. C.; Hoz, A. Carbon 2000, 38, 1641.
(c) Xu, Y.; Guo, Q. X. Heterocycles 2004, 63, 903.
(d) Das, S. K. Synlett 2004, 915.
[5] Nuchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128.
[6] Shishkov, I. V.; Rominger, F.; Hofmann, P. Organometallics 2009, 28, 1049.
[7] Ito, J.; Ujiie, S.; Nishiyama, H. Chem. Eur. J. 2010, 16, 4986.
[8] Ferrand, Y.; Maux, P. L.; Simonneaux, G. Tetrahedron: Asymmetry 2005, 16, 3829.
[9] Chen, Y.; Ruppel, J. V.; Zhang, X. P. J. Am. Chem. Soc. 2007, 129, 12074.
[10] Krawczyk, H.; Wasek, K.; Kedzia, J.; Wojciechowski, J.; Wolf, W. M. Org. Biomol. Chem. 2008, 6, 308.
[11] Rosenberg, M. L.; Vlasana, K.; Gupta, N. S.; Wragg, D., Tilset, M. J. Org. Chem. 2011, 76, 2465.
[12] Davi, M.; Lebel, H. Chem. Commun. 2008, 4974.
[13] Berkessel, A.; Kaiser, P.; Lex, J. Chem. Eur. J. 2003, 9, 4746.
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