OALib Journal期刊
ISSN: 2333-9721
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异腈参与的惰性键活化反应研究进展有机化学
DOI: 10.6023/cjoc201411035 , PP. 588-602
Keywords: C—H键活化 ,异腈 ,自由基反应 ,插入反应 ,含氮杂环
Abstract:
近年来,过渡金属催化的C—H键官能团化反应引起了广泛的关注并得到迅速发展.作为一个不可替代的合成子,异腈已被广泛应用于合成各类含氮杂环化合物.本综述介绍了异腈参与的惰性键活化反应的最新研究进展及其在有机合成中的应用,包括异腈对C—H键或N—H键的插入反应以及异腈参与的自由基氧化成环反应等.
References
[1] Peng, J.; Liu, L.; Hu, Z.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 3772.
[2] Hu, Z.; Liang, D.; Zhao, J.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 7371.
[3] Thirupathi, N.; Hari Babu, M.; Dwivedi, V.; Kant, R.; Sridhar Reddy, M. Org. Lett. 2014, 16, 2908.
[4] Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614.
[5] Lygin, A. V.; Larionov, O. V.; Korotkov, V. S.; de Meijere, A. Chem. -Eur. J. 2009, 15, 227.
[6] Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058.
[7] Basavanag, U. M. V.; Dos Santos, A.; ElKaim, L.; Gámez-Mon- ta?o, R.; Grimaud, L. Angew. Chem., Int. Ed. 2013, 52, 7194.
[8] Xia, Z.; Zhu, Q. Org. Lett. 2013, 15, 4110.
[9] Huang, X.; Xu, S.; Tan, Q.; Gao, M.; Li, M.; Xu, B. Chem. Commun. 2014, 50, 1465.
[10] Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363.
[11] Wang, H.; Yu, Y.; Hong, X.; Xu, B. Chem. Commun. 2014, 50, 13485.
[12] Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792.
[13] Wang, Q.; Dong, X.; Xiao, T.; Zhou, L. Org. Lett. 2013, 15, 4846.
[14] Cheng, Y.; Jiang, H.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 5520.
[15] Wang, R.; Jiang, H.; Cheng, Y.; Kadi, A. A.; Fun, H.-K.; Zhang, Y.; Yu, S. Synthesis 2014, 46, 2711.
[16] Zhang, B.; Studer, A. Org. Lett. 2014, 16, 1216.
[17] Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2013, 52, 13289.
[18] Zhang, B.; Studer, A. Org. Lett. 2014, 16, 3990.
[19] Sun, X.; Yu, S. Org. Lett. 2014, 16, 2938.
[20] Fu, W.; Zhu, M.; Xu, C.; Zou, G.; Wang, Z.; Ji, B. J. Fluorine Chem. 2014, 168, 50.
[21] Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643.
[22] Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164.
[23] Cheng, Y.; Yuan, X.; Jiang, H.; Wang, R.; Ma, J.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2014, 356, 2859.
[24] Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286.
[25] Tu, H.-Y.; Liu, Y.-R.; Chu, J.-J.; Hu, B.-L.; Zhang, X.-G. J. Org. Chem. 2014, 79, 9907.
[26] Yu, J.-T.; Feng, X.; Zhu, H.; Wang, L.; Jiang, Y.; Cheng, J. Org. Biomol. Chem. 2014, 12, 9257.
[27] Cao, J.-J.; Zhu, T.-H.; Wang, S.-Y.; Gu, Z.-Y.; Wang, X.; Ji, S.-J. Chem. Commun. 2014, 50, 6439.
[28] Wang, L.; Sha, W.; Dai, Q.; Feng, X.; Wu, W.; Peng, H.; Chen, B.; Cheng, J. Org. Lett. 2014, 16, 2088.
[29] Sha, W.; Yu, J.-T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 9179.
[30] Zhu, Z.-Q.; Wang, T.-T.; Bai, P.; Huang, Z.-Z. Org. Biomol. Chem. 2014, 12, 5839.
[31] Li, Z.; Fan, F.; Yang, J.; Liu, Z.-Q. Org. Lett. 2014, 16, 3396.
[32] Cao, J.-J.; Wang, X.; Wang, S.-Y.; Ji, S.-J. Chem. Commun. 2014, 50, 12892.
[33] Liu, J.; Fan, C.; Yin, H.; Qin, C.; Zhang, G.; Zhang, X.; Yi, H.; Lei, A. Chem. Commun. 2014, 50, 2145.
[34] He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451.
[35] Wang, G.; Chen, S.-Y.; Yu, X.-Q. Tetrahedron Lett. 2014, 55, 5338.
[36] Pan, C.; Han, J.; Zhang, H.; Zhu, C. J. Org. Chem. 2014, 79, 5374.
[37] Li, X.; Fang, M.; Hu, P.; Hong, G.; Tang, Y.; Xu, X. Adv. Synth. Catal. 2014, 356, 2103.
[38] Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z.-W.; Zhou, L. Green Chem. 2014, 16, 2418.
[39] Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 16, 250.
[40] Li, Y.; Qiu, G.; Ding, Q.; Wu, J. Tetrahedron 2014, 70, 4652.
[41] Gao, Y.; Wu, J.; Xu, J.; Wang, X.; Tang, G.; Zhao, Y. Asian J. Org. Chem. 2014, 3, 691.
[42] Cao, J.-J.; Zhu, T.-H.; Gu, Z.-Y.; Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2014, 70, 6985.
[43] Yang, B.; Tian, Q.; Yang, S. Chin. J. Org. Chem. 2014, 34, 717 (in Chinese). (杨斌, 田秋萍, 杨尚东, 有机化学, 2014, 34, 717.)
[44] Wang, L.; Zhu, H.; Guo, S.; Cheng, J.; Yu, J.-T. Chem. Commun. 2014, 50, 10864.
[45] Yang, X.-L.; Chen, F.; Zhou, N.-N.; Yu, W.; Han, B. Org. Lett. 2014, 16, 6476.
[46] (a) Nenajdenko, V. Isocyanide Chemistry: Applications in Synthesis and Material Science, Wiley-VCH, Weinheim, 2012. (b) D?mling, A. Chem. Rev. 2005, 106, 17. (c) Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323. (d) D?mling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083. (e) Banfi, L.; Riva, R. In Organic Reactions, Vol. 65, Ed.: Overman, L.E., Wiley, 2005.
[47] (a) Malatesta, L.; Bonati, F. Isocyanide complex of Metals, Wiley-Interscience, New York, 1969. (b) Horrocks, W.; Mann, R. Spectrochim. Acta 1963, 19, 1375. (c) Malatesta, L. Prog. Inorg. Chem. 1959, 1, 283. (d) Lazar, M.; Angelici, R. J. J. Am. Chem. Soc. 2006, 128, 10613.
[48] (a) Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094. (b) Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257. (c) Lang, S. Chem. Soc. Rev. 2013, 42, 4867. (d) Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084.
[49] Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047.
[50] Tobisu, M.; Imoto, S.; Ito, S.; Chatani, N. J. Org. Chem. 2010, 75, 4835.
[51] Zhu, C.; Xie, W.; Falck, J. R. Chem.-Eur. J. 2011, 17, 12591.
[52] Liu, Y.-J.; Xu, H.; Kong, W.-J.; Shang, M.; Dai, H.-X.; Yu, J.-Q. Nature 2014, 515, 389.
[53] Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966.
[54] Hong, X.; Wang, H.; Qian, G.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3228.
[55] Qian, G.; Hong, X.; Liu, B.; Mao, H.; Xu, B. Org. Lett. 2014, 16, 5294.
[56] Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604.
[57] Wang, Y.; Zhu, Q. Adv. Synth. Catal. 2012, 354, 1902.
[58] Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
[59] Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270.
[60] Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260.
[61] Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664.
[62] Tsukada, N.; Wada, M.; Takahashi, N.; Inoue, Y. J. Organomet. Chem. 2009, 694, 1333.
[63] Gao, M.; He, C.; Chen, H.; Bai, R.; Cheng, B.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 6958.
[64] Liu, J.; Fang, Z.; Zhang, Q.; Liu, Q.; Bi, X. Angew. Chem., Int. Ed. 2013, 52, 6953.
[65] Liu, J.; Liu, Z.; Wu, N.; Liao, P.; Bi, X. Chem.-Eur. J. 2014, 20, 2154.
[66] Fang, T.; Tan, Q.; Ding, Z.; Liu, B.; Xu, B. Org. Lett. 2014, 16, 2342.
[67] Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094.
[68] Xia, Z.; Huang, J.; He, Y.; Zhao, J.; Lei, J.; Zhu, Q. Org. Lett. 2014, 16, 2546.
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