Chinese Journal of Organic Chemistry >
Progress in C—N Bonds Formation Using t-BuONO
Received date: 2017-03-23
Revised date: 2017-04-18
Online published: 2017-05-10
Supported by
Project supported by the Research Funds of Ningbo University (No. ZX2016000706) and the K. C. Wong Magna Fund in Ningbo University.
The formation of C—N bonds by nitration is a powerful strategy for organic synthesis. Recently, the remarkable progress has been made in synthesis of nitrogen compounds using tert-butyl nitrite as nitration reagent. The present protocol, with a mild reaction condition and an excellent region selectivity, provides a green and efficient approach to construct C—N bonds. This review will summarize the recent development in this area on the basis of different substrates systems.
Key words： tert-butyl nitrite; C—N bond; nitration
Wei Wenting , Zhu Wenming , Wu Yi , Huang Yiling , Liang Hongze . Progress in C—N Bonds Formation Using t-BuONO[J]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 1916 -1923 . DOI: 10.6023/cjoc201703039
[1] Miller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
[2] Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926.
[3] Cho, H. S.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
[4] Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931.
[5] Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
[6] Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
[7] Bariwal, J.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 9283.
[8] Song, R.-J.; Xie, Y.-X. Chin. J. Chem. 2017, 35, 280.
[9] Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2015, 1195.
[10] Chen, T.; Yan, M.; Zheng, C.; Yuan, J.; Xu, S.; Chen, R.; Huang, W. Chin. J. Chem. 2015, 33, 961.
[11] Xu, S.-Y.; Chen, X.-J.; Li, J.-H.; Xu, W.-R.; Zhang, Y.-C. Chin. J. Org. Chem. 2016, 36, 1985(in Chinese). (徐树英, 陈小佳, 黎吉辉, 许文茸, 张玉苍, 有机化学, 2016, 36, 1985.)
[12] Zhao, J.-B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235(in Chinese). (赵金钵, 张前, 化学学报, 2015, 73, 1235.)
[13] Shang, X.-J.; Liu, Z.-Q. Acta Chim. Sinica 2015, 73, 1275(in Chinese). (尚筱洁, 刘忠全, 化学学报, 2015, 73, 1275.)
[14] Yuan, S.-T.; Wang, Y.-H.; Qiu, G.; Liu, J.-B. Chin. J. Org. Chem. 2017, 37, 566(in Chinese). (袁斯甜, 王艳华, 邱观音生, 刘晋彪, 有机化学, 2017, 37, 566.)
[15] Shi, M.; Cui, S.-C. Adv. Synth. Catal. 2003, 345, 1329.
[16] Stepanov, A. V.; Veselovsky, V. V. Russ. Chem. Rev. 2003, 72, 327.
[17] Hwu, J. R.; Chen, K.-L.; Ananthan, S.; Patel, H. V. Organometallics 1996, 15, 499.
[18] Maity, S.; Manna, S.; Rana, S.; Naveen, T.; Mallick, A.; Maiti, D. J. Am. Chem. Soc. 2013, 135, 3355.
[19] Taniguchi, T.; Fujii, T.; Ishibashi, H. J. Org. Chem. 2010, 75, 8126.
[20] Grenier, J. L.; Catteau, J. P.; Cotelle, P. Synth. Commun. 1999, 29, 1201.
[21] Siri, O.; Jaquinod, L.; Smith, K. M. Tetrahedron Lett. 2000, 41, 3583.
[22] Tanaka, M.; Muro, E.; Ando, H.; Xu, Q.; Fujiwara, M.; Souma, Y.; Yamaguchi, Y. J. Org. Chem. 2000, 65, 2972.
[23] Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629.
[24] Zhou, L.; Tang, S.; Qi, X.; Lin, C.; Liu, K.; Liu, C.; Lan, Y.; Lei, A. Org. Lett. 2014, 16, 3404.
[25] Tran, B. L.; Li, B.; Driess, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 2555.
[26] Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Angew. Chem., Int. Ed. 2004, 43, 1120.
[27] Zhang, W.; Ren, S. B.; Zhang, J.; Liu, Y. K. J. Org. Chem. 2015, 80, 5973.
[28] Shu, Z. B.; Ye, Y. X.; Deng, Y. F.; Zhang, Y.; Wang, J. B. Angew. Chem., Int. Ed. 2013, 52, 10573.
[29] Chen, F.; Huang, X. Q.; Li, X. Y.; Shen, T.; Zou, M. C.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 10495.
[30] Deng, G.-B.; Zhang, J.-L.; Liu, Y.-Y.; Liu, B.; Yang, X.-H.; Li, J.-H. Chem. Commun. 2015, 51, 1886.
[31] Koley, D.; Colon, O. C.; Savinov, S. N. Org. Lett. 2009, 11, 4172.
[32] Wu, X.-F.; Schranck, J.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 12462.
[33] Kilpatrick, B.; Heller, M.; Arns, S. Chem. Commun. 2013, 49, 514.
[34] Majhi, B.; Kundu, D.; Ahammed, S.; Ranu, B. C. Chem. Eur. J. 2014, 20, 9862.
[35] Liang, Y.-F.; Li, X. Y.; Wang, X. Y.; Yan, Y. P.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956.
[36] Zhao, J.; Li, P.; Xia, C.; Li, F. RSC Adv. 2015, 5, 32835.
[37] Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
[38] McDonald, R. L.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981.
[39] Prateeptongkum, S.; Jovel, I.; Jackstell, R.; Vogl, N.; Weckbecker, C.; Beller, M. Chem. Commun. 2009, 15, 1990.
[40] Taniguchi, T.; Yajima, A.; Ishibashi, H. Adv. Synth. Catal. 2011, 353, 2643.
[41] Manna, S.; Jana, S.; Saboo, T.; Maji, A.; Maiti, D. Chem. Commun. 2013, 49, 5286.
[42] Taniguchi, T.; Sugiura, Y.; Hatta, T.; Yajima, A.; Ishibashi, H. Chem. Commun. 2013, 49, 2189.
[43] Maity, S.; Naveen, T.; Sharma, U.; Maiti, D. Org. Lett. 2013, 15, 3384.
[44] Peng, X.-X.; Deng, Y.-J.; Yang, X.-L.; Zhang, L.; Yu, W.; Han, B. Org. Lett. 2014, 16, 4650.
[45] Shen, T.; Yuan, Y. Z.; Jiao, N. Chem. Commun. 2014, 50, 554.
[46] Cao, Q.; Liu, J. D.; Yu, L.; Gui, Q. W.; Chen, X.; Tan, Z. Synth. Commun. 2015, 45, 2181.
[47] Chumnanvej, N.; Katrun, P.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C. Chin. J. Chem. 2016, 34, 830.
[48] Yang, J.; Liu, Y.-Y.; Song, R.-J.; Peng, Z.-H.; Li, J.-H. Adv. Synth. Catal. 2016, 358, 2286.
[49] Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2006, 62, 5126.
[50] Trost, B. M.; Chan, V. S.; Yamamoto, D. J. Am. Chem. Soc. 2010, 132, 5186.
[51] Dutta, U.; Maity, S.; Kancherla, R.; Maiti, D. Org. Lett. 2014, 16, 6302.
[52] Yan, H.; Mao, J.; Rong, G.; Liu, D.; Zheng, Y.; He, Y. Green Chem. 2015, 17, 2723.
[53] Guo, P.; Li, H.-X.; Hao, X.-H.; Jin, D.-P.; Chen, D.-Q.; Yan, X.-B.; Wu, X.-X.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 6298.
[54] Yang, X.-H.; Ouyang, X.-H.; Wei, W.-T.; Song, R.-J., Li, J.-H. Adv. Synth. Catal. 2015, 357, 1161.
[55] Yang, X.-H.; Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2015, 357, 3849.
[56] Lin, Y. G.; Kong, W. G.; Song, Q. L. Org. Lett. 2016, 18, 3702.
[57] Lin, Y.; Song, Q. Eur. J. Org. Chem. 2016, 18, 3056.
[58] Dutta, U.; Lupton, D. W.; Maiti, D. Org. Lett. 2016, 18, 860.
[59] Chen, M.; Weng, Y.; Guo, M.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2008, 47, 2279.
[60] Liu, P.; Fukui, Y.; Tian, P.; He, Z.-T.; Sun, Z.-Y.; Wu, L.-Y.; Lin, G.-Q. J. Am. Chem. Soc. 2013, 135, 11700.
[61] Sylvester, K. T.; Chirik, P. J. J. Am. Chem. Soc. 2009, 131, 8772.
[62] Liu, Y.; Zhang, J.-L.; Song, R.-J.; Qian, P.-C.; Li, J.-H. Angew. Chem., Int. Ed. 2014, 53, 9017.
[63] Hu, M.; Liu, B.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2015, 357, 3332.
[64] Hao, X.-H.; Gao, P.; Song, X.-R.; Qiu, Y.-F.; Jin, D.-P.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2015, 51, 6839.
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