综述与进展

异腈参与的惰性键活化反应研究进展

  • 王浩 ,
  • 许斌
展开
  • a 上海大学化学系 上海 200444;
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032;
    c 华东师范大学 上海市绿色化学与化工过程绿色化重点实验室 上海 200062

收稿日期: 2014-11-22

  修回日期: 2014-12-19

  网络出版日期: 2015-01-07

基金资助

国家自然科学基金(No. 21272149)和上海市教委科研创新重点(No. 14ZZ094)资助项目.

Recent Advances in Inert Bonds Activation with Isocyanides

  • Wang Hao ,
  • Xu Bin
Expand
  • a Department of Chemistry, Shanghai University, Shanghai 200444;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062

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).

摘要

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.

本文引用格式

王浩 , 许斌 . 异腈参与的惰性键活化反应研究进展[J]. 有机化学, 2015 , 35(3) : 588 -602 . DOI: 10.6023/cjoc201411035

Abstract

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.

参考文献

[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.

文章导航

/