扩环氮杂环卡宾前体鎓盐的合成进展

doi:10.6023/cjoc201211035

摘要/Abstract

氮杂环卡宾(N-heterocyclic carbenes, NHCs)作为一种新兴配体, 在现代有机化学中有非常重要的应用. 有关NHCs的初期研究较多集中在易于合成、性质稳定的咪唑衍生五元-NHCs及其金属化合物, 近年研究发现的六元、七元等扩环-NHCs, 由于其独特的立体和化学特性而成为现代有机化学的又一研究热点. 氮杂环鎓盐去质子化是获得NHCs的常用方法, 因而扩环-NHCs前体鎓盐的合成是影响扩环-NHCs研究进展的一个重要因素, 就近年来扩环-NHCs前体鎓盐的合成进展作一综述.

关键词: 氮杂环卡宾, 扩环, 前体

As a kind of novel developed ligands, N-heterocyclic carbenes (NHCs) play very important roles in the development of modern organic chemistry. Early studies on NHCs have been mainly focused on imidazole derived five membered heterocycles, due to their easy accessibility and comparably stable properties. Recently, ring expanded NHCs, such as six- or seven-membered NHCs became another research hot spot due to their steric characteristics and chemical properties. Because deprotonation of the heterocyclic onium salt precursors is by far the most commonly used method to access NHCs, the synthesis of the precursors remains a key factor affecting the development of ring expanded NHCs. This review will summarize the progress on the synthesis of ring expanded NHC precursors.

Key words: N-heterocyclic carbene, ring expanded, precursor

引用此文

杨亮茹, 魏栋, 买文鹏, 毛璞. 扩环氮杂环卡宾前体鎓盐的合成进展[J]. 有机化学, 2013, 33(05): 943-953.

Yang Liangru, Wei Dong, Mai Wenpeng, Mao Pu. Development on the Synthesis of Ring Expanded N-Heterocyclic Carbene Precursors[J]. Chin. J. Org. Chem., 2013, 33(05): 943-953.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Wanzlick, H.-W. Angew. Chem., Int. Ed. 1962, 1, 75.
[2] Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
[3] (a) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109(8), 3612.
(b) Samojlowicz, C.; Bieniek, M.; Grela, K. Chem. Rev. 2009, 109(8), 3708.
(c) Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109(8), 3677.
(d) Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Chem. Rev. 2009, 109(8), 3859.
(e) 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.)
[4] (a) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122.
(b) Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940.
(c) Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445.
(d) Budagumpi, S.; Haque, R. A.; Salman, A. W. Coord. Chem. Rev. 2012, 256, 1787.
(e) Jiang, L.; Li, Z. N.; Zhao, D. F. Chin. J. Org. Chem. 2010, 30, 200 (in Chinese).
(姜岚, 李争宁, 赵德峰, 有机化学, 2010, 30, 200.)
(f) Li, J. Y.; Peng, J. J.; Li, X. N.; Ma, L.; Bai, Y.; Zhang, G. D.; Lai, G. Q. Chin. J. Org. Chem. 2010, 30, 1468 (in Chinese).
(厉嘉云, 彭家建, 李小年, 马磊, 白赢, 张国栋, 来国桥, 有机化学, 2010, 30, 1468.)
(g) Yu, Y. F.; Shan, F. J.; Li, Z. N.; Jiang, L. Chin. J. Org. Chem. 2011, 31, 443 (in Chinese).
(于艳飞, 单凤军, 李争宁, 姜岚, 有机化学, 2011, 31, 443.)
(h) Gao, Y. X.; Zhou, H. Y.; Li, Y. Q.; Wang, J. X. Chin. J. Org. Chem. 2012, 32, 1493 (in Chinese).
(高艳炫, 周宏勇, 李云庆, 王家喜, 有机化学, 2012, 32, 1493.)
(i) Xu, Q.; Shi. M. Acta Chim. Sinica 2012, 70, 1593 (in Chinese). (徐琴, 施敏, 化学学报, 2012, 70, 1593.)
[5] (a) Spallek, M. J.; Riedel, D.; Rominger, F.; Hashmi, A. S. K.; Trapp, O. Organometallics 2012, 31, 112.
(b) Hashmi, A. S. K.; Lothschütz, C.; Böhling, C.; Rominger, F. Organometallics 2011, 30, 2411.
(c) Hashmi, A. S. K.; Lothschütz, C.; Graf, K.; H?ffner, T.; Schuster, A.; Rominger, F. Adv. Synth. Catal. 2011, 353, 1407.
[6] (a) Benhamou, L.; Chardon, E.; Lavigne, G. Chem. Rev. 2011, 111, 2705.
(b) Mao, P.; Cai, Y. J.; Xiao, Y. M.; Yang, L. R.; Xue, Y.; Song, M. P. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2418.
[7] Orelli, L. R.; García, M. B.; Perillo, I. A. Heterocycles 2000, 53, 2437.
[8] (a) Mayr, M.; Wurst, K.; Ongania, K. H.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 1256.
(b) Yang, L.; Mayr, M.; Wurst, K.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 5761.
(c) Bantu, B.; Wang, D.; Wurst, K.; Buchmeiser, M. R. Tetrahedron 2005, 61, 12145.
(d) Imlinger, N.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2005, 690, 4433.
(e) Zhang, Y.; Wang, D.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2005, 690, 5728.
(f) Mayr, M.; Buchmeiser, M. R. Macromol. Rapid Commun. 2004, 25, 231.
(g) Kumar, P. S.; Wurst, K.; Buchmeiser, M. R. Chem. Asian J. 2009, 4, 1275.
(h) Bantu, B.; Pawar, G. M.; Wurst, K.; Decker, U.; Axel M. Schmidt, A. M.; Buchmeiser, M. R. Eur. J. Inorg. Chem. 2009, 1970.
(i) Bantu, B, Pawar, G. M.; Decker, U.; Wurst, K.; Schmidt, A. M.; Buchmeiser, M. R. Chem. Eur. J. 2009, 15, 3103.
[9] Bisceglia, J. A.; Garcia, M. B.; Massa, R.; Magri, M. L.; Zani, M.; Gutkind, G. O.; Orelli, L. R. J. Heterocycl. Chem. 2004, 85.
[10] (a) Mao, P.; Liu, X.; Yang, L.; Yuan, J.; Song, M. Acta Crystallogr. 2011, E67, m62.
(b) Mao, P.; Yang, L.; Xiao, Y.; Yuan, J.; Liu, X.; Song, M. J. Organomet. Chem. 2012, 705, 39.
[11] (a) Ahdulla, R. F.; Brinheyer, R. S. Tetrahedron 1979, 35, 1675.
(b) Cetinkaya, E; Hitchcock, P. B.; Jasim, H. A.; Lappert, M. F.; Spyropoulos, K. J. Chem. Soc., Perkin. Trans. 1 1992, 561.
[12] (a) Alici, B.; Cetinkaya, E.; Cetinkaya, B. Heterocycles 1997, 45, 29.
(b) Mercan, D.; ?etinkaya, E.; ?etinkaya, B. J. Organomet. Chem. 2011, 696, 1359.
[13] (a) Alici, B; Özdemir, ì.; Gürbüz, N.; ?etinkaya, E.; ?etinkaya, B. Heterocycles 2005, 65, 1439.
(b) Özdemir, ì.; Demir, S.; ?etinkaya, B. ARKIVOC 2007, xiii, 71.
[14] Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. J. Chem. Commun. 1999, 241.
[15] Bazinet, P.; Yap, G. P. A; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 13314.
[16] Bazinet, P.; Ong, T.-G.; O'Brien, J. S.; Lavoie, N.; Bell, E.; Yap, G. P. A.; Korobkov, I.; Richeson, D. S. Organometallics 2007, 26, 2885.
[17] Herrmann, W. A.; Schneider, S. K.; Öfele, K.; Sakamoto, M.; Herdtweck, E. J. Organomet. Chem. 2004, 689, 2441.
[18] 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.
[19] Yun, J.; Marinez, E. R.; Grubbs, R. H. Organometallics 2004, 23, 4172.
[20] Paczal, A; Bényei, A. C.; Kotschy, A. J. Org. Chem. 2006, 71, 5969.
[21] Iglesias, M.; Beetstra, D. J.; Stasch, A.; Horton, P. N.; Hursthouse, M. B.; Coles, S. J.; Cavell, K. J.; Dervisi, A.; Fallis, I. A. Organometallics 2007, 26, 4800.
[22] Özdemir, I.; Gürbüz, N.; Gök, Y.; ?etinkaya, B. Heteroat. Chem. 2008, 19, 82.
[23] Khramov, D. M.; Rosen, E. L.; Lynch, V. M.; Bielawski, C. W. Angew. Chem., Int. Ed. 2008, 47, 2267.
[24] (a) Siemeling, U.; F?rber, C.; Bruhn, C. Chem. Commun. 2009, 98.
(b) Siemeling, U.; F?rber, C.; Leibold, M.; Bruhn, C.; Mücke, P.; Winter, R. F.; Sarkar, B.; Hopffgarten, M. V.; Frenking, G. Eur. J. Inorg. Chem. 2009, 31, 4607.
[25] (a) Reddy, P. V. G.; Tabassum, S.; Blanrue, A.; Wilhelm, R. Chem. Commun. 2009, 5910.
(b) Yang, Z. H.; Wang, L. X.; Zhou, Z. H.; Zhou, Q. L.; Tang, C. C. Tetrahedron: Asymmetry 2001, 12, 1579.
(c) He, K.; Zhou, Z.; Wang, L.; Li, K.; Zhao, G.; Zhou, Q.; Tang, C. Tetrahedron 2004, 60, 10505.
[26] Newman, P. D.; Cavell, K. J.; Kariuki, B. M. Organometallics 2010, 29, 2724.
[27] Busacca, C. A.; Lorenz, J. C.; Grinberg, N.; Haddad, N.; Lee, H.; Li, Z.; Liang, M.; Reeves, D.; Saha, A.; Varsolona, R.; Senanayake, C. H. Org. Lett. 2008, 10, 341.
[28] (a) Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008.
(b) Davis, E. M.; Nanninga, T. N.; Tjiong, H. I.; Winkle, D. D. Org. Process Res. Dev. 2005, 9, 843.
(c) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417.
[29] (a) Scarborough, C. C.; Grady, M. J. W.; Guzei, I. A.; Gandhi, B. A.; Bunel, E. E.; Stahl, S. S. Angew. Chem., Int. Ed. 2005, 44, 5269.
(b) Scarborough, C. C.; Popp, B. V.; Guzei, I. A.; Stahl, S. S. J. Organomet. Chem. 2005, 690, 6143.
[30] (a) Scarborough, C. C.; Guzei, I. A.; Stahl, S. S. Dalton Trans. 2009, 2284.
(b) Scarborough, C. C.; Bergant, A; Sazama, G. T.; Guzei, I. A.; Spencer, L. C.; Stahl, S. S. Tetrahedron 2009, 65, 5084.
(c) Rogers, M. M.; Wendlandt, J. E.; Guzei, I. A.; Stahl, S. S. Org. Lett. 2006, 8, 2257.
[31] Roberts, R. M. J. Org. Chem. 1949, 14, 277.
[32] Jazzar, R.; Liang, H.; Donnadieu, B.; Bertrand, G. J. Organomet. Chem. 2006, 691, 3201.
[33] Frey, G. D.; Song, M.; Bourg, J. B.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Chem. Commun. 2008, 4711.
[34] (a) Iglesias, M.; Beetstra, D. J.; Knight, J. C.; Ooi, L. L.; Stasch, A.; Coles, S.; Male, L.; Hursthouse, M. B.; Cavell, K. J.; Dervisi, A.; Fallis, I. A. Organometallics 2008, 27, 3279.
(b) Lu, W. Y.; Cavell, K. J.; Wixey, J. S.; Kariuki, B. Organometallics 2011, 30, 5649.
[35] Pr?sang, C.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2005, 127, 10182.
[36] (a) Forster, T. D.; Krahulic, K. E.; Tuononen, H. M.; McDonald, R.; Parvez, M.; Roesler, R. Angew. Chem., Int. Ed. 2006, 45, 6356.
(b) Krahulic, K. E.; Tuononen, H. M.; Parvez, M.; Roesler, R. J. Am. Chem. Soc. 2009, 131, 5858.
[37] (a) César, V.; Lugan, N.; Lavigne, G. J. Am. Chem. Soc. 2008, 130, 11286.
(b) César, V.; Lugan, N.; Lavigne, G. Chem. Eur. J. 2010, 16, 11432.
[38] César, V.; Lugan, N.; Lavigne, G. Eur. J. Inorg. Chem. 2010, 361.
[39] Hudnall, T. W.; Tennyson, A. G.; Bielawski, C. W. Organometallics 2010, 29, 4569.
[40] Hudnall, T. W.; Bielawski, C. W. J. Am. Chem. Soc. 2009, 131, 16039.
[41] Blake, G. A.; Moerdyk, J. P.; Bielawski, C. W. Organometallics 2012, 31, 3373.
[42] Mushinski, R. M.; Squires, B. M.; Sincerbox, K. A.; Hudnall. T. W. Organometallics 2012, 31, 4862.
[43] Martin, D.; Lassauque, N.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2012, 51, 6172.
[44] Hobbs, M. G.; Knapp, C. J.; Welsh, P. T.; Borau-Garcia, J.; Ziegler, T.; Roesler, R. Chem. Eur. J. 2010, 16, 14520.
[45] Lewis, R. T.; Motherwell, W. B. Tetrahedron 1992, 48, 1484.
[46] Makhloufi, A.; Frank, W.; Ganter, C. Organometallics 2012, 31, 2001.