Chinese Journal of Organic Chemistry >
Recent Advances in Inert Bonds Activation with Isocyanides
Received date: 2014-11-22
Revised date: 2014-12-19
Online published: 2015-01-07
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272149), and the Innovation Program of Shanghai Municipal Education Commission (No. 14ZZ094).
Transition-metal-catalyzed C—H functionalization has attracted tremendous interest as a valuable tool for the construction of heterocycles. As a unique building block, isocyanides have been widely used in the synthesis of various nitrogen-containing heterocycles through multi-component Passerini and Ugi reactions. This review highlights the recent progress in inert bonds activation with isocyanides, including C—H bond or N—H bond insertion of isocyanides and radical oxidative annulation of isocyanides.
Wang Hao , Xu Bin . Recent Advances in Inert Bonds Activation with Isocyanides[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 588 -602 . DOI: 10.6023/cjoc201411035
[1] (a) Nenajdenko, V. Isocyanide Chemistry: Applications in Synthesis and Material Science, Wiley-VCH, Weinheim, 2012. (b) Dömling, A. Chem. Rev. 2005, 106, 17. (c) Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323. (d) Dömling, 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.
[2] (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.
[3] (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.
[4] Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047.
[5] Tobisu, M.; Imoto, S.; Ito, S.; Chatani, N. J. Org. Chem. 2010, 75, 4835.
[6] Zhu, C.; Xie, W.; Falck, J. R. Chem.-Eur. J. 2011, 17, 12591.
[7] Liu, Y.-J.; Xu, H.; Kong, W.-J.; Shang, M.; Dai, H.-X.; Yu, J.-Q. Nature 2014, 515, 389.
[8] Peng, J.; Liu, L.; Hu, Z.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 3772.
[9] Hu, Z.; Liang, D.; Zhao, J.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 7371.
[10] Thirupathi, N.; Hari Babu, M.; Dwivedi, V.; Kant, R.; Sridhar Reddy, M. Org. Lett. 2014, 16, 2908.
[11] Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614.
[12] Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966.
[13] Hong, X.; Wang, H.; Qian, G.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3228.
[14] Qian, G.; Hong, X.; Liu, B.; Mao, H.; Xu, B. Org. Lett. 2014, 16, 5294.
[15] Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604.
[16] Wang, Y.; Zhu, Q. Adv. Synth. Catal. 2012, 354, 1902.
[17] Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
[18] Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270.
[19] Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260.
[20] Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664.
[21] Lygin, A. V.; Larionov, O. V.; Korotkov, V. S.; de Meijere, A. Chem. -Eur. J. 2009, 15, 227.
[22] Tsukada, N.; Wada, M.; Takahashi, N.; Inoue, Y. J. Organomet. Chem. 2009, 694, 1333.
[23] Gao, M.; He, C.; Chen, H.; Bai, R.; Cheng, B.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 6958.
[24] Liu, J.; Fang, Z.; Zhang, Q.; Liu, Q.; Bi, X. Angew. Chem., Int. Ed. 2013, 52, 6953.
[25] Liu, J.; Liu, Z.; Wu, N.; Liao, P.; Bi, X. Chem.-Eur. J. 2014, 20, 2154.
[26] Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058.
[27] Basavanag, U. M. V.; Dos Santos, A.; ElKaim, L.; Gámez-Mon- taño, R.; Grimaud, L. Angew. Chem., Int. Ed. 2013, 52, 7194.
[28] Xia, Z.; Zhu, Q. Org. Lett. 2013, 15, 4110.
[29] Huang, X.; Xu, S.; Tan, Q.; Gao, M.; Li, M.; Xu, B. Chem. Commun. 2014, 50, 1465.
[30] Fang, T.; Tan, Q.; Ding, Z.; Liu, B.; Xu, B. Org. Lett. 2014, 16, 2342.
[31] Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094.
[32] Xia, Z.; Huang, J.; He, Y.; Zhao, J.; Lei, J.; Zhu, Q. Org. Lett. 2014, 16, 2546.
[33] Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363.
[34] Wang, H.; Yu, Y.; Hong, X.; Xu, B. Chem. Commun. 2014, 50, 13485.
[35] Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792.
[36] Wang, Q.; Dong, X.; Xiao, T.; Zhou, L. Org. Lett. 2013, 15, 4846.
[37] Cheng, Y.; Jiang, H.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 5520.
[38] Wang, R.; Jiang, H.; Cheng, Y.; Kadi, A. A.; Fun, H.-K.; Zhang, Y.; Yu, S. Synthesis 2014, 46, 2711.
[39] Zhang, B.; Studer, A. Org. Lett. 2014, 16, 1216.
[40] Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2013, 52, 13289.
[41] Zhang, B.; Studer, A. Org. Lett. 2014, 16, 3990.
[42] Sun, X.; Yu, S. Org. Lett. 2014, 16, 2938.
[43] Fu, W.; Zhu, M.; Xu, C.; Zou, G.; Wang, Z.; Ji, B. J. Fluorine Chem. 2014, 168, 50.
[44] Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643.
[45] Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164.
[46] Cheng, Y.; Yuan, X.; Jiang, H.; Wang, R.; Ma, J.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2014, 356, 2859.
[47] Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286.
[48] Tu, H.-Y.; Liu, Y.-R.; Chu, J.-J.; Hu, B.-L.; Zhang, X.-G. J. Org. Chem. 2014, 79, 9907.
[49] Yu, J.-T.; Feng, X.; Zhu, H.; Wang, L.; Jiang, Y.; Cheng, J. Org. Biomol. Chem. 2014, 12, 9257.
[50] Cao, J.-J.; Zhu, T.-H.; Wang, S.-Y.; Gu, Z.-Y.; Wang, X.; Ji, S.-J. Chem. Commun. 2014, 50, 6439.
[51] Wang, L.; Sha, W.; Dai, Q.; Feng, X.; Wu, W.; Peng, H.; Chen, B.; Cheng, J. Org. Lett. 2014, 16, 2088.
[52] Sha, W.; Yu, J.-T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 9179.
[53] Zhu, Z.-Q.; Wang, T.-T.; Bai, P.; Huang, Z.-Z. Org. Biomol. Chem. 2014, 12, 5839.
[54] Li, Z.; Fan, F.; Yang, J.; Liu, Z.-Q. Org. Lett. 2014, 16, 3396.
[55] Cao, J.-J.; Wang, X.; Wang, S.-Y.; Ji, S.-J. Chem. Commun. 2014, 50, 12892.
[56] Liu, J.; Fan, C.; Yin, H.; Qin, C.; Zhang, G.; Zhang, X.; Yi, H.; Lei, A. Chem. Commun. 2014, 50, 2145.
[57] He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451.
[58] Wang, G.; Chen, S.-Y.; Yu, X.-Q. Tetrahedron Lett. 2014, 55, 5338.
[59] Pan, C.; Han, J.; Zhang, H.; Zhu, C. J. Org. Chem. 2014, 79, 5374.
[60] Li, X.; Fang, M.; Hu, P.; Hong, G.; Tang, Y.; Xu, X. Adv. Synth. Catal. 2014, 356, 2103.
[61] Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z.-W.; Zhou, L. Green Chem. 2014, 16, 2418.
[62] Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 16, 250.
[63] Li, Y.; Qiu, G.; Ding, Q.; Wu, J. Tetrahedron 2014, 70, 4652.
[64] Gao, Y.; Wu, J.; Xu, J.; Wang, X.; Tang, G.; Zhao, Y. Asian J. Org. Chem. 2014, 3, 691.
[65] Cao, J.-J.; Zhu, T.-H.; Gu, Z.-Y.; Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2014, 70, 6985.
[66] 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.)
[67] Wang, L.; Zhu, H.; Guo, S.; Cheng, J.; Yu, J.-T. Chem. Commun. 2014, 50, 10864.
[68] Yang, X.-L.; Chen, F.; Zhou, N.-N.; Yu, W.; Han, B. Org. Lett. 2014, 16, 6476.
/
| 〈 |
|
〉 |
