过渡金属杂小环的扩环反应研究进展

doi:10.6023/cjoc201403050

摘要/Abstract

过渡金属杂环化合物特别是过渡金属杂小环化合物（成环原子数小于6个）在金属有机化学和配位化学领域中具有重要的地位，它们是许多过渡金属催化反应包括烯烃复分解反应、炔烃聚合反应的中间体. 通常过渡金属杂小环化合物具有较大的环张力，因此极易与不饱和化合物反应生成环张力较小的扩环产物. 针对过渡金属杂小环化学研究现状，综述了几类典型的过渡金属杂三、四、五元环的扩环反应.

关键词: 过渡金属, 杂环化合物, 扩环反应

Metallacycles, especially those small rings, play an important role in the field of organometallic and coordination chemistry. They are considered as reactive intermediates in metal promoted or catalyzed reactions including olefin metathesis reactions and alkyne polymerization reactions. Due to the high ring strain, small metallacycles can easily react with unsaturated compounds to produce ring expansion products with lower ring strain. To further understand the importance of small metallacycle intermediates in the catalytic reactions and synthesis methodology, the ring expansion reactions of several typical three-, four- and five-membered metallacycles is summarize.

Key words: transition metal, heterocyclic compounds, ring-expansion reaction

引用此文

卓庆德, 王铜道, 周小茜, 张弘. 过渡金属杂小环的扩环反应研究进展[J]. 有机化学, 2014, 34(8): 1471-1486.

Zhuo Qingde, Wang Tongdao, Zhou Xiaoxi, Zhang Hong. Progresses of Ring Expansion Reaction of Small Transitional Metallacyclic Compounds[J]. Chin. J. Org. Chem., 2014, 34(8): 1471-1486.

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

分享此文

参考文献

[1] Selected reviews of metallacycles:
(a) Li, Z.; Zhao, B.; Xi, Z. Chemistry 2002, (2), 78 (in Chinese).
(李志平, 赵炳筠, 席振峰, 化学通报, 2002, (2), 78.)
(b) Xi, Z.; Li, Z. Top. Organomet. Chem. 2004, 8, 27.
(c) Negishi, E. Dalton Trans. 2005, 827.
(d) Erker, G.; Kehr, G.; Fröhlich, R. Coord. Chem. Rev. 2006, 250,36.
(e) Rosenthal, U.; Burlakov, V. V.; Bach, M. A.; Beweries, T. Chem. Soc. Rev. 2007, 719.
(f) Suzuki, N.; Hashizume, D. Coord. Chem. Rev. 2010, 254, 1307.
(g) Chen, C.; Xi, C. Chin. Sci. Bull. 2010, 55, 3235.
(h) Beweries, T.; Haehnel, M.; Rosenthal, U. Catal. Sci. Technol. 2013, 3, 18.
(i) Wang, Q.; Lin, C.; Xi, Z. Chin. J. Org. Chem. 2010, 30, 157 (in Chinese).
(王奇峰, 林辰, 席振峰, 有机化学, 2010, 30, 157.)
(j) Mao, K.; Fu, X.; Liu, D.; Li, S.; Liu, Y. Chin. J. Org. Chem. 2013, 33, 780 (in Chinese).
(毛可彬, 付晓平, 刘丹, 李石, 刘元红, 有机化学, 2013, 33, 780.)
[2] (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
(b) Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746.
[3] (a) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
(b) Choi, S.-K.; Gal, Y.-S.; Jin, S.-H.; Kim, H. K. Chem. Rev. 2000, 100, 1645.
[4] (a) Dewar, M. J. S. Bull. Soc. Chim. Fr. 1951, 18, C71.
(b) Chatt, J.; Duncanson, L. A. J. Chem. Soc. 1953, 2939.
[5] Frenking, G.; Fröhlich, N. Chem. Rev. 2000, 100, 717.
[6] Tsuchiya, K.; Kondo, H.; Nagashima H. Organometallics, 2007, 26, 1044.
[7] Yamazaki, H.; Aoki, K.; Yamamoto, Y.; Wakatsuki, Y. J. Am. Chem. Soc. 1975, 97, 3546.
[8] Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
[9] Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1986, 108, 7411.
[10] Vaughan, G. A.; Sofield, C. D.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1989, 111, 5491.
[11] Buijink, J. K. F. K.,; Kloetstra, K. R.; Meetsma, A.; Teuben, J. H. Organometallics 1996, 15, 2523.
[12] Beweries, T.; Fischer, C.; Peitz, S.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Heller, D.; Rosenthal, U. J. Am. Chem. Soc. 2009, 131, 4463.
[13] Mansel, S.; Thomas, D.; Lefeber, C.; Heller, D.; Kempe, R.; Baumann, W.; Rosenthal, U. Organometallics 1997, 16, 2886.
[14] Zhang, S.; Zhang, W.-X.; Zhao, J.; Xi, Z. J. Am. Chem. Soc. 2010, 132, 14042.
[15] Lee, L. W. M.; Piers, W. E.; Parvez, M.; Rettig, S. J.; Young, V. G. Organometallics 1999, 18, 3904.
[16] (a) Schrock, R. R.; Pedersen, S. F.; Churchill, M. R.; Ziller, J. W. Organometallics 1984, 3, 1574.
(b) Zhu, J.; Jia, G.; Lin, Z. Organometallics 2006, 25, 1812.
(c) Mortreux A.; Coutelier, O. J. Mol. Catal. A: Chem. 2006, 254, 96.
[17] Loewe, C.; Shklover V.; Berke, H. Organometallics 1991, 10, 3396.
[18] (a) Padolik, L. L.; Gallucci, J. C.; Wojcicki, A. J. Am. Chem. Soc. 1993, 115, 9986.
(b) Plantevin, V.; Gallucci, J. C.; Wojcicki, A. Inorg. Chim. Acta 1994, 222, 199.
(c) Plantevin, V.; Wojcicki, A. J. Organomet. Chem. 2004, 689, 2000.
[19] (a) Plantevin, V.; Wojcicki, A. J. Organomet. Chem. 2004, 689, 2013.
(b) Wu, H.-P.; Weakley, T. J. R.; Haley, M. M. Chem. Eur. J. 2005, 11, 1191.
[20] Recent reviews of metallabenzenes:
(a) Paneque, M.; Poveda, M. L.; Rendóon, N. Eur. J. Inorg. Chem. 2011, 19.
(b) Jia, G. Coord. Chem. Rev. 2007, 251, 2167.
(c) Bleeke, J. R. Acc. Chem. Res. 2007, 40, 1035.
(d) Wright, L. J. Dalton Trans. 2006, 1821.
(e) Landorf, C. W.; Haley, M. M. Angew. Chem., Int. Ed. 2006, 45, 3914.
(f) Jia, G. Acc. Chem. Res. 2004, 37, 479.
(g) He, G.; Xia, H.; Jia, G. Chin. Sci. Bull. 2004, 49, 1543.
(h) Bleeke, J. R. Chem. Rev. 2001, 101, 1205.
[21] Clark, G. R.; Lu, G.-L.; Roper, W. R.; Wright L. J. Organometallics 2007, 26, 2167.
[22] Poon, K. C.; Liu, L. X.; Guo, T. X.; Li, J.; Sung, H. H. Y.; Williams, I. D.; Lin, Z. Y.; Jia, G. C. Angew. Chem., Int. Ed. 2010, 49, 2759.
[23] (a) Masuda, T.; Higashimura, T. Acc. Chem. Res. 1984, 17, 51.
(b) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737.
(c) Fox, H. H.; Wolf, M. O.; O'Dell, R.; Lin, B. L.; Schrock, R. R.; Wrighton, M. S. J. Am. Chem. Soc. 1994, 116, 2827.
[24] (a) Katz, T. J. Angew. Chem., Int. Ed. 2005, 44, 3010.
(b) Diver, S. T. Coord. Chem. Rev. 2007, 251, 671.
(c) Mori, M. Materials 2010, 3, 2087.
(d) Li, J.; Lee, D. Eur. J. Org. Chem. 2011, 4269.
[25] Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
[26] (a) Shono, T.; Kurashige, R.; Mukaiyama, R.; Tsubouchi, A.; Takeda, T. Chem. Eur. J. 2007, 13, 4074.
(b) O'Connor, J. M.; Baldridge, K. K.; Vélez, C. L.; Rheingold, A. L.; Moore, C. E. J. Am. Chem. Soc. 2013, 135, 8826.
[27] (a) Doxsee, K. M.; Mouser, J. K. M. Organometallics 1990, 9, 3012.
(b) Doxsee, K. M.; Mouser, J. K. M.; Farahi, J. B. Synlett 1992, 13.
[28] Doxsee, K. M.; Mouser, J. K. M. Tetrahedron Lett. 1991, 32, 1687.
[29] Meinhart, J. D.; Grubbs, R. H. Bull. Chem. Soc. Jpn. 1988, 61, 171.
[30] Heijden, H. V. D.; Hessen, B. Inorg. Chim. Acta 2003, 345, 27.
[31] (a) Stewart, I. C.; Douglas, C. J.; Grubbs, R. H. Org. Lett. 2008, 10, 441.
(b) Geny, A.; Leboeuf, D.; Rouquié, G.; Vollhardt, K. P. C.; Malacria, M.; Gandon, V.; Aubert, C. Chem. Eur. J. 2007, 13, 5408.
[32] Holland, R. L.; Bunker, K. D.; Chen, C. H.; DiPasquale, A. G.; Rheingold, A. L.; Baldridge, K. K.; O'Connor, J. M. J. Am. Chem. Soc. 2008, 130, 10093.
[33] Meinhart, J. D.; Santarsiero, B. D.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 3318.
[34] Wakatsuki, Y.; Miya, S.-Y.; Yamazaki, H. J. Chem. Soc., Dalton. Trans. 1986, 1201.
[35] Werner, H.; Heinemann, A.; Windmüiiller, B.; Steinert, P. Chem. Ber. 1996, 129, 903.
[36] Beckhaus, R.; Sang, J.; Wagner, T.; Ganter, B. Organometallics 1996, 15, 1176.
[37] Holland, R. L.; O'Connor, J. M. Organometallics 2009, 28, 394.
[38] Doxsee, K. M.; Farahi, J. B. J. Am. Chem. Soc. 1988, 110, 7239.
[39] Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589.
[40] Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716.
[41] Hartwig, J. F.; Bergman, R. G. Andersen R. A. Organometallics 1991, 10, 3344.
[42] Ajulu, F. A.; Carmichael, D.; Hitchcock, P. B.; Mathey, F.; Meidine, M. F.; Nixon, J. F.; Ricard L.; Riley, M. L. J. Chem. Soc., Chem. Commun. 1992, 750.
[43] Tanabe, M.; Horie, M. Osakada, K. Organometallics, 2003, 22, 373.
[44] Cristóobal, C.; Hernáandez, Y. A.; Lóopez-Serrano, J.; Paneque, M.; Petronilho, A.; Poveda, M. L.; Salazar, V.; Vattier, F.; ÁAlvarez, E.; Maya, C.; Carmona, E. Chem. Eur. J. 2013, 19, 4003.
[45] (a) Takahashi, T.; Xi, Z.; Obora, Y.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 2665.
(b) Xi, Z.; Fischer, R.; Hara, R.; Sun, W.-H.; Obora, Y.; Suzuki, N.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 1997, 119, 12842.
[46] (a) Sun, X.; Wang, C.; Li, Z.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2004, 126, 7172.
(b) Zhang, W.-X.; Zhang, S.; Sun, X.; Nishiura, M.; Hou, Z.; Xi, Z. Angew. Chem., Int. Ed. 2009, 48, 7227.
(c) Zhang, S.; Sun, X.; Zhang, W.-X.; Xi, Z. Chem. Eur. J. 2009, 15, 12608.
(d) Zhang, S.; Zhang, W.-X.; Xi, Z. Chem. Eur. J. 2010, 16, 8419.
(e) Zhang, S.; Zhao, J.; Zhang, W.-X.; Xi, Z. Org. Lett. 2011, 13, 1626.
(f) Zhang, S.; Zhang, W.-X.; Zhao, J.; Xi, Z. Chem. Eur. J. 2011, 17, 2442.
(g) Zhao, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Organometallics 2011, 30, 3464.
(h) Zhao, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Organometallics 2012, 31, 8370.
(i) Zhao, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Organometallics 2014, 33, 8.
[47] (a) Yu, T.; Deng, L.; Zhao, C.; Li, Z.; Xi, Z. Tetrahedron Lett. 2003, 44, 677.
(b) Liu, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Organometallics 2009, 28, 413.
[48] Yu, T.; Sun, X.; Wang, C.; Deng, L.; Xi, Z. Chem. Eur. J. 2005, 11, 1895.
[49] Zhang, W.-X.; Zhang, S.; Xi, Z. Acc. Chem. Res. 2011, 44, 541.
[50] Zhao, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Coord. Chem. Rev. 2014, 270, 2.
[51] (a) Xi, Z.; Li, Z. Top. Organomet. Chem. 2004, 8, 27.
(b) Xi, Z. Top. Catal. 2005, 35, 63.
(c) Takahashi, T.; Kuzuba, Y.; Kong, F.; Nakajima, K.; Xi, Z. J. Am. Chem. Soc. 2005, 127, 17188.
(d) Leng, L.; Xi, C.; Shi, Y.; Guo, B. Synlett 2003, 183.
(e) Chen, C.; Xi, C.; Lai, C.; Wang, R.; Hong, X. Eur. J. Org. Chem. 2004, 647.
(f) Leng, L.; Xi, C.; Chen, C.; Lai, C. Tetrahedron Lett. 2004, 45, 595.
(g) Chen, C.; Xi, C.; Liu, Y.; Hong, X. J. Org. Chem. 2006, 71, 5373.
(h) Chen, C.; Yan, X.; Xi, C. Synth. Commun. 2010, 40, 570.
(i) Zhou, Y.; Yan, X.; Chen, C.; Xi, C. Organometallics 2013, 32, 6182.
[52] (a) Shi, L.; Zhou, L.; Kanno, K.-I.; Takahashi, T. J. Heterocycl. Chem. 2011, 48, 517.
(b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
(c) Liu, J.; Zhang, W.-X.; Guo, X.; Hou, Z.; Xi, Z. Organometallics 2007, 26, 6812.
[53] Xi, Z.; Sato, K.; Gao, Y.; Lu, J.; Takahashi, T. J. Am. Chem. Soc. 2003, 125, 9568.
[54] (a) Xi, Z.; Fan, H.; Mito, S.; Takahashi, T. J. Organomet. Chem. 2003, 682, 108.
(b) Lu, J.; Mao, G.; Zhang, W.; Xi, Z. Chem. Commun. 2005, 4848.
(c) Hu, Q.; Lu, J.; Wang, C.; Wang, C.; Xi, Z. Tetrahedron 2007, 63, 6614.
[55] (a) Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950.
(b) Zhao, C.; Li, P.; Cao, X.; Xi, Z. Chem. Eur. J. 2002, 8, 4292.
(c) Xi, Z.; Guo, R.; Mito, S.; Yan, H.; Kanno, K.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2003, 68, 1252.
(d) Chen, C.; Xi, C.; Jiang, Y.; Hong, X. J. Am. Chem. Soc. 2005, 127, 8024.
(e) Chen, C.; Xi, C.; Ai, Z.; Hong, X. Org. Lett. 2006, 8, 4055.
[56] Xi, Z.; Huo, S.; Noguchi, Y.; Takahashi, T. Chem. Lett. 2000, 218.
[57] (a) Chin, C. S.; Kim, M.; Lee, H.; Noh, S.; Ok, K. M. Organometallics 2002, 21, 4785.
(b) Chin, C. S.; Lee, H. Chem. Eur. J. 2004, 10, 4518.
[58] Elliott, G. P.; Roper, W. R.; Waters, J. M. J. Chem. Soc., Chem. Commun. 1982, 811.
[59] Clark, G. R.; Johns, P. M.; Roper, W. R.; Wright, J. L. Organometallics 2008, 27, 451.
[60] Dalebrook, A. F.; Wright, L. J. Organometallics 2009, 28, 5536.
[61] Clark, G. R.; Johns, P. M.; Roper, W. R. Sohnel, T.; Wright, L. J. Organometallics 2011, 30, 129.
[62] (a) Zhou, S.; Liu, D.; Liu, Y. Organometallics 2004, 23, 5900.
[63] Lin, Y.; Gong, L.; Xu, H.; He, X.; Wen, T.B.; Xia, H. Organometallics 2009, 28, 1524.
[64] (a) Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int. Ed. 2009, 48, 5500.
(b) Fu, X.; Liu, Y.; Li, Y. Organometallics 2010, 29, 3012.
(c) Fu, X.; Yu, S.; Fan, G.; Liu Y.; Li, Y. Organometallics 2012, 31, 531.
(d) Yu, S.; You, X.; Liu Y. Chem. Eur. J. 2012, 18, 13936.
(e) You, X.; Yu, S.; Liu Y. Organometallics 2013, 32, 5273.
[65] Pellny, P.-M.; Kirchbauer, F. G.; Burlakov, V. V.; Baumann, W.; Spannenberg, A.; Rosenthal, U. J. Am. Chem. Soc. 1999, 121, 8313.
[66] Bender, G.; Kehr, G.; Frohlich, R.; Petersen, J. L.; Erker, G. Chem. Sci. 2012, 3, 3534.
[67] Wang, T.; Zhu, J.; Han, F.; Zhou, C.; Chen, H.; Zhang, H.; Xia, H. Angew. Chem., Int. Ed. 2013, 52, 13361.
[68] (a) Liu, Y.; Gao, H.; Zhou, S. Angew. Chem., Int. Ed. 2006, 45, 4163.
(b) Zhou, Y.; Chen, J.; Zhao, C.; Wang, E.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 5326.
[69] (a) Coperet, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695.
(b) Li, P.; Xi, Z.; Takahashi, T. Chin. J. Chem. 2001, 19, 45.
(c) Zhao, C.; Yan, J.; Xi, Z. J. Org. Chem. 2003, 68, 4355.
(d) Zhao, C.; Lu, J.; Yan, J.; Xi, Z. Tetrahedron Lett. 2003, 44, 6895.
(e) Zhao, C.; Lu, J. Li, Z.; Xi, Z. Tetrahedron 2004, 60, 1417.
[70] Gong, L.; Wu, L.; Lin, Y.; Zhang, H.; Yang, F.; Wen, T. B.; Xia, H. Dalton Trans. 2007, 4122.
[71] (a) Mao, K.; Fan, G.; Liu, Y.; Li, S.; Xu, Y.; Dan, L. Beilstein J. Org. Chem. 2013, 9, 621.
(b) Chen, J.; Liu, Y. Organometallics 2010, 29, 505.
[72] (a) Liu, B.; Zhao, Q.; Wang, H.; Zeng, B.; Cao, X.; Xia, H. Sci. China Chem. 2013, 56, 1105.
(b) Zhang, C.; Zhang, H.; Wei, A.; He, X.; Xia, H. Acta Chim. Sinica 2013, 71, 1373 (in Chinese).
(张春红, 张弘, 魏爱琳, 何旭敏, 夏海平, 化学学报, 2013, 71, 1373.)
[73] Zhang, C.; Zhang, H.; Zhang, L.; Wen, T. B.; He, X.; Xia, H. Organometallics 2013, 32, 3738.
[74] (a) Liu, B.; Wang, H.; Xie, H.; Zeng, B.; Chen, J.; Tao, J.; Wen, T. B.; Cao, Z.; Xia, H. Angew. Chem., Int. Ed. 2009, 48, 5430.
(b) Liu, B.; Zhao, Q.; Wang, H.; Chen, J.; Cao, X.; Cao, Z.; Xia, H. Chin. J. Chem. 2012, 30, 2158.
[75] Liu, B.; Xie, H. J; Wang, H.; Wu, L.; Zhao, Q.; Chen, J.; Wen, T. B.; Cao, Z.; Xia, H. Angew. Chem., Int. Ed. 2009, 48, 5461.
[76] (a) Zhao, Q.; Gong, L.; Xu, C.; Zhu, J.; He, X.; Xia, H. Angew. Chem., Int. Ed. 2011, 50, 1354.
(b) Zhu, C.; Cao, X.; Xia, H. Chin. J. Org. Chem. 2013, 33, 657.
(c) Zhao, Q.; Cao, X.-Y.; Wen, T. B.; Xia, H. Chem. Asian J. 2013, 8, 269.
[77] Zhao, Q.; Zhu, J.; Huang, Z.; Cao, X.-Y.; Xia, H. Chem. Eur. J. 2012, 18, 11597.
[78] Chen, J; Zhang, C.; Xie, T.; Wen, T. B.; Zhang, H.; Xia, H. Organometallics 2013, 32, 3993.