Research Progress in the Cycloaddition Reactions of Nitroso Compounds

doi:10.6023/cjoc201604001

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 1994-2010.DOI: 10.6023/cjoc201604001 Previous Articles Next Articles

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亚硝基化合物环加成反应的研究进展

李东君^a, 武彦芳^b, 常宏宏^a, 高文超^a, 魏文珑^a, 李兴^a

a 太原理工大学化学化工学院太原 030024;
b 大同大学化学与环境工程学院大同 037008

收稿日期:2016-04-01 修回日期:2016-05-13 发布日期:2016-06-08
通讯作者: 魏文珑, 李兴 E-mail:lixing@tyut.edu.cn
基金资助:
山西省自然科学基金（Nos.2012021007-2）资助项目.

Research Progress in the Cycloaddition Reactions of Nitroso Compounds

Li Dongjun^a, Wu Yanfang^b, Chang Honghong^a, Gao Wenchaoa^a, Wei Wenlong^a, Li Xing^a

a College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024;
b College of Chemistry and Environmental Engineering, Datong University, Datong 037008

Received:2016-04-01 Revised:2016-05-13 Published:2016-06-08
Supported by:
Project supported by the Natural Science Foundation of Shanxi Province (Nos.2012021007-2).

Cite this article

Li Dongjun, Wu Yanfang, Chang Honghong, Gao Wenchaoa, Wei Wenlong, Li Xing. Research Progress in the Cycloaddition Reactions of Nitroso Compounds[J]. Chin. J. Org. Chem., 2016, 36(9): 1994-2010.

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[1] (a) Wang, W.; Lu, X. H.; Dong, X. C.; Zhao, W. L. Chin. J. Org. Chem. 2015, 35, 137(in Chinese). (王雯, 陆秀宏, 董肖椿, 赵伟利, 有机化学, 2015, 35, 137.) (b) Wu, Y. Q.; Yu, L. Y.; Zhang, Q.; Li, L. D. Chin. J. Org. Chem. 2015, 35, 724(in Chinese). (吴玉芹, 于凉云, 张奇, 李立冬, 有机化学, 2015, 35, 724.) (c) Zheng, J. F.; Xie, Z. Q.; Chen, X. J.; Huang, P. Q. Acta Chim. Sinica 2015, 73, 705. (d) Cheng, G.; Yang, D. Q. Chin. J. Org. Chem. 2015, 35, 2023(in Chinese). (程果, 杨定乔, 有机化学, 2015, 35, 2023.) (e) Li, G. D.; Hu, H. Y.; Kan, Y. H.; Ma, K. R. Chin. J. Org. Chem. 2014, 34, 903(in Chinese). (李国栋, 胡华友, 阚玉和, 马奎蓉, 有机化学, 2014, 34, 903.) (f) Li, Q. H.; Huang, R.; Wang, C. J. Acta Chim. Sinica 2014, 72, 830(in Chinese). (李清华, 黄蓉, 王春江, 化学学报, 2014, 72, 830.) (g) Sun, L. H.; Liang, Z. Q.; Ye, S. Acta Chim. Sinica 2014, 72, 841(in Chinese). (孙利辉, 梁志钦, 叶松, 化学学报, 2014, 72, 841.) (h) Xie, M. S.; Wu, X. X.; Wang, G.; Lin, L. L.; Feng, X. M. Acta Chim. Sinica 2014, 72, 856(in Chinese). (谢明胜, 武晓霞, 王刚, 林丽丽, 冯小明, 化学学报, 2014, 72, 856.) (i) Zhou, R.; Xiao, W.; Yin, X.; Zhan, G.; Chen, Y. C. Acta Chim. Sinica 2014, 72, 862(in Chinese). (周容, 肖微, 尹祥, 詹固, 陈应春, 化学学报, 2014, 72, 862.) (j) Yang, L. J.; Ma, J. A. Acta Chim. Sinica 2016, 74, 130(in Chinese). (杨丽军, 马军安, 化学学报, 2016, 74, 130.)
[2] Dochnahl, M.; Fu, G. C. Angew. Chem. Int. Ed. 2009, 48, 2391.
[3] Wang, T.; Huang, X. L.; Ye, S. Org. Biomol. Chem. 2010, 8, 5007.
[4] Chatterjee, I.; Jana, C. K.; Steinmetz, M.; Grimme, S.; Studer, A. Adv. Synth. Catal. 2010, 352, 945.
[5] Kang, J. Y.; Bugarin, A.; Connell, B. T. Chem. Commun. 2008, 3522.
[6] Yang, L.; Tan, B.; Wang, F.; Zhong, G. J. Org. Chem. 2009, 74, 1744.
[7] Chatterjee, I.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 11257.
[8] Chen, C. H.; Tsai, Y. C.; Liu, R. S. Angew. Chem., Int. Ed. 2013, 52, 4599.
[9] Zhan, M.; Zhang, S.; Huang, Z.; Xi, Z. Chem. Asian J. 2015, 10, 862.
[10] Liu, R. S.; Ghorpade, S. M.; Jadhav, P. D. Chem. Eur. J. 2016, 22, 1
[11] Arribas, C.; Carreño, M. C.; García-Ruano, J. L.; Rodríguez, J. F.; Santos, M.; Sanz-Tejedor, M. A. Org. Lett. 2000, 2, 3165.
[12] Miller, C. A; Batey, R. A. Org. Lett. 2004, 6, 699.
[13] Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128.
[14] Calvet, G.; Guillot, R.; Blanchard, N.; Kouklovsky, C. Org. Biomol. Chem. 2005, 3, 4395.
[15] Yamamoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 7082.
[16] Jana, C. K.; Studer, A. Angew. Chem., Int. Ed. 2007, 46, 6542.
[17] Jana, C. K.; Grimme, S.; Studer, A. Chem. Eur. J. 2009, 15, 9078.
[18] Monbaliu, J. C.; Marchand-Brynaert, J. Tetrahedron Lett. 2008, 49, 1839.
[19] Jana, C. K.; Studer, A. Chem. Eur. J. 2008, 14, 6326.
[20] Yang, B.; Miller, P. A.; Möllmann, U.; Miller, M. J. Org. Lett. 2009, 11, 2828.
[21] Monbaliu, J. C.; Tinant, B.; Marchand-Brynaert, J. J. Org. Chem. 2010, 75, 5478.
[22] Monbaliu, J. C. M.; Cukalovic, A.; Marchand-Brynaert, J.; Stevens, C. V. Tetrahedron Lett. 2010, 51, 5830.
[23] Yang, B.; Zöllner, T.; Gebhardt, P.; Möllmann, U.; Miller, M. J. Org. Biomol. Chem. 2010, 8, 691.
[24] Chaiyaveij, D.; Cleary, L.; Batsanov, A. S.; Marder, T. B.; Shea, K. J.; Whiting, A. Org. Lett. 2011, 13, 3442.
[25] Jenkins, N. E.; Ware Jr, R. W.; Atkinson, R. N.; King, S. B. Synth. Commun. 2000, 30, 947.
[26] Flower, K. R.; Lightfoot, A. P.; Wan, H.; Whiting, A. J. Chem. Soc., Perkin Trans. 12002, 18, 2058.
[27] Frazier, C. P.; Bugarin, A.; Engelking, J. R.; Read de Alaniz, J. Org. Lett. 2012, 14, 3620.
[28] Anand, A.; Bhargava, G.; Singh, P.; Mehra, S.; Kumar, V.; Mahajan, M. P.; Bisetty, K. Lett. Org. Chem. 2012, 9, 411.
[29] Berti, F.; Di Bussolo, V.; Pineschi, M. J. Org. Chem. 2013, 78, 7324.
[30] Samoshin, A. V.; Hawker, C. J.; Read de Alaniz, J. ACS Macro Lett. 2014, 3, 753.
[31] Eberlin, L.; Carboni, B.; Whiting, A. J. Org. Chem. 2015, 80, 6574.
[32] Chaiyaveij, D.; Batsanov, A. S.; Fox, M. A.; Marder, T. B.; Whiting, A. J. Org. Chem. 2015, 80, 9518.
[33] Pous, J.; Courant, T.; Bernadat, G.; Iorga, B. I.; Blanchard, F.; Masson, G. J. Am. Chem. Soc. 2015, 137, 11950.
[34] Maji, B.; Yamamoto, H. J. Am. Chem. Soc. 2015, 137, 15957.
[35] Han, R.; Qi, J.; Gu, J.; Ma, D.; Xie, X.; She, X. ACS Catal. 2013, 3, 2705.
[36] Xu, Z. J.; Zhu, D.; Zeng, X.; Wang, F.; Tan, B.; Hou, Y.; Lv, Y.; Zhong, G. Chem. Commun. 2010, 46, 2504.
[37] Reddy, A. R.; Guo, Z.; Siu, F. M.; Lok, C. N.; Liu, F.; Yeung, K. C.; Zhou, C. Y.; Che, C. M. Org. Biomol. Chem. 2012, 10, 9165.
[38] Molander, G. A.; Cavalcanti, L. N. Org. Lett. 2013, 15, 3166.
[39] Chen, H.; Wang, Z.; Zhang, Y.; Huang, Y. J. Org. Chem. 2013, 78, 3503.
[40] Reddy, A. R.; Zhou, C. Y.; Che, C. M. Org. Lett. 2014, 16, 1048.
[41] Pagar, V. V.; Liu, R. S. Angew. Chem., Int. Ed. 2015, 54, 4923.
[42] Chakrabarty, S.; Chatterjee, I.; Wibbeling, B.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 5964.
[43] Vemula, N., Stevens, A. C.; Schon, T. B.; Pagenkopf, B. L. Chem. Commun. 2014, 50, 1668.
[44] Vemula, N.; Pagenkopf, B. L. Eur. J. Org. Chem. 2015, 4900.
[45] Suga, H.; Shi, X. L.; Ibata, T. Bull. Chem. Soc. Jpn. 1998, 71, 1231.
[46] Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G. Org. Lett. 2008, 10, 4585.
[47] Marwaha, A.; Singh, P.; Mahajan, M. P. Tetrahedron 2006, 62, 5474.
[48] de los Santos, J. M.; Ignacio, R.; Aparicio, D.; Palacios, F.; Ezpeleta, J. M. J. Org. Chem. 2009, 74, 3444.
[49] Kondacs, L. A.; Pilipecz, M. V.; Mucsi, Z.; Balázs, B.; Gáti, T.; Nyerges, M.; Dancsó, A.; Nemes, P. Eur. J. Org. Chem. 2015, 6872.
[50] Yoon, S. C.; Kim, K. J.; Park, Y. J. J. Org. Chem. 2001, 66, 7334.
[51] Shatzmiller, S.; Lidor, R.; Bahar, E.; Goldberg, I. Lebigs Ann. Chem. 1991, 851.
[52] Paulini, K.; Reißig, H. U. Chem. Ber. 1994, 127, 685.
[53] de los Santos, J. M.; Ignacio, R.; Es Sbai, Z.; Aparicio, D.; Pa-lacios, F. J. Org. Chem. 2014, 79, 7607.
[54] Wabnitz, T. C.; Saaby, S.; Jørgensen, K. A. Org. Biomol. Chem. 2004, 2, 828.
[55] Penoni, A.; Volkmann, J.; Nicholas, K. M. Org. Lett. 2002, 4, 699.
[56] Penoni, A.; Palmisano, G.; Broggini, G.; Kadowaki, A.; Nicholas, K. M. J. Org. Chem. 2006, 71, 823.
[57] Tibiletti, F.; Simonetti, M.; Nicholas, K. M.; Palmisano, G.; Parravicini, M.; Imbesi, F.; Tollari, S.; Penoni, A. Tetrahedron 2010, 66, 1280.
[58] Murru, S.; Gallo, A. A.; Srivastava, R. S. ACS Catal. 2010, 1, 29.
[59] Murru, S.; Gallo, A. A.; Srivastava, R. S. Eur. J. Org. Chem. 2011, 2035.
[60] Pagar, V. V.; Jadhav, A. M.; Liu, R. S. J. Am. Chem. Soc. 2011, 133, 20728. Otley, K. D.; Ellman, J. A. J. Org. Chem. 2014, 79, 8296.

亚硝基化合物环加成反应的研究进展

Research Progress in the Cycloaddition Reactions of Nitroso Compounds

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