多咪唑盐合成的N-杂环卡宾金属配合物研究进展

doi:10.6023/cjoc201307055

摘要/Abstract

N-杂环卡宾金属配合物具有良好的化学稳定性和催化活性，一直是有机化学研究领域中的热点. 咪唑盐作为N-杂环卡宾的前体，其制备容易，结构多样的特点为构建拓扑结构的N-杂环卡宾金属配合物提供了基础. 主要针对近年来由环状多咪唑盐、非环状多咪唑盐为配体与金属进行组装，或以咪唑盐与P/N 配体与金属共同组装，或经过异腈分布合成法形成的具有特殊柱状、笼状、环状、“分子方”和“分子矩形”等结构的多N-杂环卡宾金属配合物的合成，结构及物理化学性质进行归纳总结，并对其研究前景进行了展望.

关键词: N-杂环卡宾, 多咪唑盐, 金属配合物, 超分子, 结构

Owing to the excellent chemical stability and catalytic activity, N-heterocyclic carbene (NHC) complexes have always been the hotspot in the field of organic chemistry. Imidazolium salts are the precursors of NHCs, and their easy preparation and structure diversity properties make them useful for the generation of NHC complexes with topology structures. In this paper, the recent progress of synthesis, structure and physicochemical properties of NHC complexes with cylindrical, cage-like, macrocyclic, square and rectangular molecular structures which are synthesized by poly-imidazolium salts is summarized and reviewed.

Key words: N-heterocyclic carbene, poly-imidazolium salts, metal complexes, supramolecular, structure

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林彩霞, 郭琳, 李庆山, 张正之, 袁耀锋, 徐凤波. 多咪唑盐合成的N-杂环卡宾金属配合物研究进展[J]. 有机化学, 2014, 34(2): 239-266.

Lin Caixia, Guo Lin, Li Qingshan, Zhang Zhengzhi, Yuan Yaofeng, Xu Fengbo. Recent Progress of N-Heterocyclic Carbene Complexes Synthesized by Poly-imidazolium Salts[J]. Chin. J. Org. Chem., 2014, 34(2): 239-266.

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参考文献

[1] Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.

[2] Kühl, O. Functionalised N-Heterocyclic Carbene Complexes, John Wiley & Sons Ltd., Chicester, 2010.

[3] Liu, Q-X.; Li, Z.-M. Chemistry 2004, 10, 715 (in Chinese). (柳清湘; 李正名, 化学通报, 2004, 10, 715.)

[4] (a) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122. (b) de Frémont, P.; Marion, N.; Nolan, S. P. Coord. Chem. Rev. 2009, 253, 862.

[5] (a) Velazquez, H. D.; Verpoort, F. Chem. Soc. Rev. 2012, 41, 7032. (b) Nolan, S. P. Acc. Chem. Res. 2010, 44, 91. (c) Credendino, R.; Falivene, L.; Cavallo, L. J. Am. Chem. Soc. 2012, 19, 8127. (d) Zhang, R.; Xu, Q.; Shi, M. Acta Chim. Sinica 2012, 70, 1593 (in Chinese). (张睿; 徐琴; 施敏, 化学学报, 2012, 70, 1593.) (e) Cai, X.; Xie, B. Chin. Appl. Chem. 2013, 30, 123 (in Chinese). (蔡小华; 谢兵, 应用化学, 2013, 30, 123.) (f) Chen, Y.; Kong, L. Chin. J. Org. Chem. 2012, 32, 511 (in Chinese). (承勇; 孙礼林, 有机化学, 2012, 32, 511.) (g) He, T.; Wang, M.; Li, P.; Wang, L. Chin. J. Chem. 2012, 30, 979. (h) Zhang, R.; Wang, D.; Xu, Q.; Jiang, J.; Shi, M. Chin. J. Chem. 2012, 30, 1295. (i) Qu, M.-N.; He, J.-M. Chin. J. Org. Chem. 2011, 31, 1388 (in Chinese). (屈孟男, 何金梅, 有机化学, 2011, 31, 1388.)

[6] (a) Boydston, A. J.; Williams, K. A.; Bielawski, C. W. J. Am. Chem. Soc. 2005, 127, 12496. (b) Boydston, A. J.; Bielawski, C. W. Dalton Trans. 2006, 4073. (c) Tennyson, A. G.; Kamplain, J. W.; Bielawski, C. W. Chem. Commun. 2009, 2124. (d) Mercs, L.; Neels, A.; Stoeckli-Evans, H.; Albrecht, M. Dalton Trans. 2009, 7168.

[7] (a) Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Chem. Rev. 2009, 109, 3859. (b) Ray, S.; Mohan, R.; Singh, J. K.; Samantaray, M. K.; Shaikh, M. M.; Panda, D.; Ghosh, P. J. Am. Chem. Soc. 2007, 129, 15042. (c) Hickey, J. L.; Ruhayel, R. A.; Barnard, P. J.; Baker, M. V.; Berners-Price, S. J.; Filipovska, A. J. Am. Chem. Soc. 2008, 130, 12570.

[8] Liu, Q.-X.; Li, Z.-M. Chem. Res. Appl. 2005, 17, 147 (in Chinese). (柳清湘; 李正名, 化学研究与应用, 2005, 17, 147.)

[9] Rit, A.; Pape, T.; Hepp, A.; Hahn, F. E. Organometallics 2011, 30, 334.

[10] (a) Mata, J. A.; Poyatos, M.; Peris, E. Coord. Chem. Rev. 2007, 251, 841. (b) Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677.

[11] Baker, M. V.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Chem. Soc., Dalton Trans. 2001, 111.

[12] Baker, M. V.; Brown, D. H.; Simpson, P. V.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Organomet. Chem. 2006, 691, 5845.

[13] Baker, M. V.; Brayshaw, S. K.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Organomet. Chem. 2005, 690, 2312.

[14] (a) Baker, M. V.; Brown, D. H.; Haque, R. A.; Skelton, B. W.; White, A. H. Dalton Trans. 2004, 3756. (b) Barnard, P. J.; Baker, M. V.; Berners-Price, S. J.; Skelton, B. W.; White, A. H. Dalton Trans. 2004, 1038.

[15] Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151.

[16] Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561.

[17] Baker, M. V.; Brown, D. H.; Heath, C. H.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Org. Chem. 2008, 73, 9340.

[18] Barnard, P. J.; Wedlock, L. E.; Baker, M. V.; Berners-Price, S. J.; Joyce, D. A.; Skelton, B. W.; Steer, J. H. Angew. Chem., Int. Ed. 2006, 45, 5966.

[19] Melaiye, A.; Sun, Z.; Hindi, K.; Milsted, A.; Ely, D.; Reneker, D. H.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 2005, 127, 2285.

[20] Radloff, C.; Gong, H.-Y.; Schulte to Brinke, C.; Pape, T.; Lynch, V. M.; Sessler, J. L.; Hahn, F. E. Chem.-Eur. J. 2010, 16, 13077.

[21] Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 700.

[22] Garrison, J. C.; Simons, R. S.; Talley, J. M.; Wesdemiotis, C.; Tessier, C. A.; Youngs, W. J. Organometallics 2001, 20, 1276.

[23] Garrison, J. C.; Simons, R. S.; Tessier, C. A.; Youngs, W. J. J. Organomet. Chem. 2003, 673, 1.

[24] Baker, M. V.; Skelton, B. W.; White, A. H.; Williams, C. C. Organometallics 2002, 21, 2674.

[25] Wang, D.; Zhang, B.; He, C.; Wu, P.; Duan, C. Chem. Commun. 2010, 46, 4728.

[26] Hahn, F. E.; Radloff, C.; Pape, T.; Hepp, A. Chem.-Eur. J. 2008, 14, 10900.

[27] Schulte to Brinke, C.; Pape, T.; Hahn, F. E. Dalton Trans. 2013, 42, 7330.

[28] McKie, R.; Murphy, J.; Park, S.; Spicer, M.; Zhou, S.-z. Angew. Chem., Int. Ed. 2007, 46, 6525.

[29] Lu, Z.; Cramer, S. A.; Jenkins, D. M. Chem. Sci. 2012, 3, 3081.

[30] Hiraoka, S.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2004, 126, 1214.

[31] (a) Rit, A.; Pape, T.; Hahn, F. E. J. Am. Chem. Soc. 2010, 132, 4572. (b) Rit, A.; Pape, T.; Hahn, F. E. Organometallics 2011, 30, 6393.

[32] Maity, R.; Rit, A.; Schulte to Brinke, C.; Daniliuc, C. G.; Hahn, F. E. Chem. Commun. 2013, 49, 1011.

[33] Ahamed, B. N.; Dutta, R.; Ghosh, P. Inorg. Chem. 2013, 8, 4269.

[34] Dias, H. V. R.; Jin, W. Tetrahedron Lett. 1994, 35, 1365.

[35] Nakai, H.; Tang, Y.; Gantzel, P.; Meyer, K. Chem. Commun. 2003, 24.

[36] (a) Kernbach, U.; Ramm, M.; Luger, P.; Fehlhammer, W. P. Angew. Chem., Int. Ed. 1996, 35, 310. (b) Fränkel, R.; Kernbach, U.; Bakola-Christianopoulou, M.; Plaia, U.; Suter, M.; Ponikwar, W.; Nöth, H.; Moinet, C.; Fehlhammer, W. P. J. Organomet. Chem. 2001, 617～618, 530.

[37] Fränkel, R.; Birg, C.; Kernbach, U.; Habereder, T.; Nöth, H.; Fehlhammer, W. P. Angew. Chem., Int. Ed. 2001, 40, 1907.

[38] Tubaro, C.; Biffis, A.; Scattolin, E.; Basato, M. Tetrahedron 2008, 64, 4187.

[39] Hu, X. L.; Tang, Y. J.; Gantzel, P.; Meyer, K. Organometallics 2003, 22, 612.

[40] Hu, X.; Castro-Rodriguez, I.; Olsen, K.; Meyer, K. Organometallics 2004, 23, 755.

[41] Hu, X.; Castro-Rodriguez, I.; Meyer, K. Organometallics 2003, 22, 3016.

[42] Hu, X.; Castro-Rodriguez, I.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 12237.

[43] Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978.

[44] (a) Quezada, C. A.; Garrison, J. C.; Panzner, M. J.; Tessier, C. A.; Youngs, W. J. Organometallics 2004, 23, 4846. (b) Matsumoto, K.; Matsumoto, N.; Ishii, A.; Tsukuda, T.; Hasegawa, M.; Tsubomura, T. Dalton Trans. 2009, 6795.

[45] Jean-Baptiste dit Dominique, F.; Gornitzka, H.; Hemmert, C. J. Organomet. Chem. 2008, 693, 579.

[46] Cure, J.; Poteau, R.; Gerber, I. C.; Gornitzka, H.; Hemmert, C. Organometallics 2012, 31, 619.

[47] Baron, M.; Tubaro, C.; Biffis, A.; Basato, M.; Graiff, C.; Poater, A.; Cavallo, L.; Armaroli, N.; Accorsi, G. Inorg. Chem. 2012, 51, 1778.

[48] (a) Liu, Q.-X.; Yang, X.-Q.; Zhao, X.-J.; Ge, S.-S.; Liu, S.-W.; Zang, Y.; Song, H.-b.; Guo, J.-H.; Wang, X.-G. CrystEngComm 2010, 12, 2245. (b) Liu, Q. X.; Zhang, W.; Zhao, X. J.; Zhao, Z. X.; Shi, M. C.; Wang, X. G. Eur. J. Org. Chem. 2013, 1253.

[49] Hemmert, C.; Poteau, R.; dit Dominique, F. J.-B.; Ceroni, P.; Bergamini, G.; Gornitzka, H. Eur. J. Inorg. Chem. 2012, 3892.

[50] Paulose, T. A. P.; Wu, S.-C.; Olson, J. A.; Chau, T.; Theaker, N.; Hassler, M.; Quail, J. W.; Foley, S. R. Dalton Trans. 2012, 41, 251.

[51] Gil-Rubio, J.; Cámara, V.; Bautista, D.; Vicente, J. Inorg. Chem. 2013, 7, 4071.

[52] Papini, G.; Pellei, M.; Lobbia, G. G.; Burini, A.; Santini, C. Dalton Trans. 2009, 6985.

[53] Wang, J.; Gao, L.; Gan, Z.; Meng, F. Chin. J. Org. Chem. 2008, 28, 775 (in Chinese). (王君文, 高林英, 甘志刚, 孟繁慧, 有机化学, 2008, 28, 775.)

[54] (a) Wang, J.-W.; Song, H.-B.; Li, Q.-S.; Xu, F.-B.; Zhang, Z.-Z. Inorg. Chim. Acta 2005, 358, 3653. (b) Wang, J.-W.; Li, Q.-S.; Xu, F.-B.; Song, H.-B.; Zhang, Z.-Z. Eur. J. Org. Chem. 2006, 2006, 1310.

[55] Wang, J.-W.; Gao, L.-Y.; Meng, F.-H.; Jiao, J.; Ding, L.-Y.; Zhang, L.-F. J. Inclusion Phenom. Macrocyclic Chem. 2012, 73, 119.

[56] (a) Liu, Q.-X.; Zhao, X.-J.; Wu, X.-M.; Guo, J.-H.; Wang, X.-G. J. Organomet. Chem. 2007, 692, 5671. (b) Liu, Q.-X.; Yu, J.; Zhao, X.-J.; Liu, S.-W.; Yang, X.-Q.; Li, K.-Y.; Wang, X.-G. CrystEngComm 2011, 13, 4086.

[57] (a) Jean-Baptiste dit Dominique, F.; Gornitzka, H.; Sournia-Saquet, A.; Hemmert, C. Dalton Trans. 2009, 340. (b) Chen, J. C. C.; Lin, I. J. B. J. Chem. Soc., Dalton Trans. 2000, 839.

[58] Haque, R. A.; Ghdhayeb, M. Z.; Salman, A. W.; Budagumpi, S.; Khadeer Ahamed, M. B.; Abdul Majid, A. M. S. Inorg. Chem. Commun. 2012, 22, 113.

[59] Iqbal, M. A.; Haque, R. A.; Budagumpi, S.; Khadeer Ahamed, M. B.; Abdul Majid, A. M. S. Inorg. Chem. Commun. 2013, 28, 64.

[60] Haque, R. A.; Iqbal, M. A.; Budagumpi, S.; Khadeer Ahamed, M. B.; Abdul Majid, A. M. S.; Hasanudin, N. Appl. Organomet. Chem. 2013, 27, 214.

[61] Raynal, M.; Cazin, C. S. J.; Vallee, C.; Olivier-Bourbigou, H.; Braunstein, P. Chem. Commun. 2008, 3983.

[62] (a) Haque, R. A.; Salman, A. W.; Guan, T. S.; Abdallah, H. H. J. Organomet. Chem. 2011, 696, 3507. (b) Salman, A. W.; Haque, R. A.; Budagumpi, S. Polyhedron 2012, 42, 18.

[63] (a) Liu, Q.-X.; Wang, H.; Zhao, X.-J.; Yao, Z.-Q.; Wang, Z.-Q.; Chen, A.-H.; Wang, X.-G. CrystEngComm 2012, 14, 5330. (b) Liu, Q.-X.; Zhao, L.-X.; Zhao, X.-J.; Zhao, Z.-X.; Wang, Z.-Q.; Chen, A.-H.; Wang, X.-G. J. Organomet. Chem. 2013, 731, 35.

[64] Liu, Q.-X.; Chen, A.-H.; Zhao, X.-J.; Zang, Y.; Wu, X.-M.; Wang, X.-G.; Guo, J.-H. CrystEngComm 2011, 13, 293.

[65] Saito, S.; Saika, M.; Yamasaki, R.; Azumaya, I.; Masu, H. Organometallics 2011, 30, 1366.

[66] Wan, X.; Xu, F.; Zhang, Z.; Song, H. Z. Anorg. Allg. Chem. 2011, 637, 34.

[67] Liu, Y.-S.; Wan, X.-J.; Xu, F.-B. Organometallics 2009, 28, 5590.

[68] Lin, C.-X.; Kong, X.-F.; Xu, F.-B.; Zhang, Z.-Z.; Yuan, Y.-F. Z. Anorg. Allg. Chem. 2013, 639, 881.

[69] Liu, Q.-X.; Yao, Z.-Q.; Zhao, X.-J.; Zhao, Z.-X.; Wang, X.-G. Organometallics 2013, 32, 3493.

[70] Han, Y.-F.; Jin, G.-X.; Hahn, F. E. J. Am. Chem. Soc. 2013, 135, 9263.

[71] Wan, X.-J.; Xu, F.-B.; Li, Q.-S.; Song, H.-B.; Zhang, Z.-Z. Inorg. Chem. Commun. 2005, 8, 1053.

[72] (a) Liu, Q.-X.; Yao, Z.-Q.; Zhao, X.-J.; Chen, A.-H.; Yang, X.-Q.; Liu, S.-W.; Wang, X.-G. Organometallics 2011, 30, 3732. (b) Wan, X.-J.; Xu, F.-B.; Li, Q.-S.; Song, H.-B.; Zhang, Z.-Z. Organometallics 2005, 24, 6066.

[73] Zhang, X.; Qiu, Y.; Rao, B.; Luo, M. Organometallics 2009, 28, 3093.

[74] Zhang, W.; Zhang, X.; Luo, M. Chin. J. Chem. 2012, 30, 1423.

[75] (a) Liu, N.; Liu, C.; Jin, Z. Chin. J. Org. Chem. 2012, 32, 860 (in Chinese). (刘宁; 刘春; 金子林, 有机化学, 2012, 32, 860.) (b) Karimi, B.; Akhavan, P. F. Chem. Commun. 2011, 47, 7686. (c) Fihri, A.; Luart, D.; Len, C.; Solhy, A.; Chevrin, C.; Polshettiwar, V. Dalton Trans. 2011, 40, 3116.

[76] (a) Liu, B.; Chen, W.; Jin, S. Organometallics 2007, 26, 3660. (b) Zhang, X.; Xi, Z.; Liu, A.; Chen, W. Organometallics 2008, 27, 4401.

[77] Gu, S.-J.; Huang, J.-J.; Chen, W.-Z. J. Org. Chem. 2013, 33, 713 (in Chinese). (顾绍金, 黄菁菁, 陈万芝, 有机化学, 2013, 33, 713.)

[78] Budagumpi, S.; Haque, R. A.; Salman, A. W.; Ghdhayeb, M. Z. Inorg. Chim. Acta 2013, 392, 61.

[79] Mokhtari, B.; Pourabdollah, K.; Dalali, N. J. Inclusion Phenom. Macrocyclic Chem. 2011, 69, 1.

[80] (a) Fahlbusch, T.; Frank, M.; Maas, G.; Schatz, J. Organometallics 2009, 28, 6183. (b) Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem. 2004, 607.

[81] Dinarès, I.; Garcia de Miguel, C.; Font-Bardia, M.; Solans, X.; Alcalde, E. Organometallics 2007, 26, 5125.

[82] (a) Lin, C.-X.; Kong, X.-F.; Li, Q.; Zhang, Z.-Z.; Yuan, Y.; Xu, F.-B. CrystEngComm 2013, 15, 6948. (b) Qin, D.-B.; Zeng, X.-X.; Li, Q.-X.; Xu, F.-B.; Song, H.-B.; Zhang, Z.-Z. Chem. Commun. 2007, 147.

[83] Hahn, F. E.; Radloff, C.; Pape, T.; Hepp, A. Organometallics 2008, 27, 6408.

[84] Radloff, C.; Weigand, J. J.; Hahn, F. E. Dalton Trans. 2009, 9392.

[85] Conrady, F. M.; Froehlich, R.; Brinke, C. S. T.; Pape, T.; Hahn, F. E. J. Am. Chem. Soc. 2011, 133, 11496.