SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 04: 780 - 791

DOI: https://doi.org/10.6023/cjoc201211023

综述与进展

锆-苯炔参与的金属杂环的形成及其在有机合成中的应用

  • 毛可彬 ,
  • 付晓平 ,
  • 刘丹 ,
  • 李石 ,
  • 刘元红
展开
  • a 沈阳化工大学化学工程学院 沈阳 110142;
    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

收稿日期: 2012-11-13

  修回日期: 2012-11-26

  网络出版日期: 2012-12-07

基金资助

国家自然科学基金(Nos. 21072208, 21125210, 21121062)和国家重点基础研究发展计划(973计划, No. 2011CB808700)资助项目.

收起

Construction of Metallacycles via Zirconium-Benzyne Complexes and Its Application in Organic Synthesis

  • Mao Kebin ,
  • Fu Xiaoping ,
  • Liu Dan ,
  • Li Shi ,
  • Liu Yuanhong
Expand
  • a Colledge of Chemical Engineering, Shenyang University of Chemical Technology, Shenyang 110142;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2012-11-13

  Revised date: 2012-11-26

  Online published: 2012-12-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21072208, 21125210, 21121062) and the Major State Basic Research Development Program (973 Program, No. 2011CB808700).

Fold

摘要

锆-苯炔是一类非常重要且具有高度反应活性的金属有机配合物. 其与烯、炔、醛、酮、腈等不饱和底物反应时, 通过调节底物的取代基、化学计量比、配体结构以及反应条件等, 可以得到多种形式的锆杂环类化合物. 该锆杂环进一步与亲电试剂反应可以构筑结构丰富多样的有机化合物. 对锆-苯炔的合成方法及其参与的金属杂环的形成与后续反应等方面进行了综述, 并对锆-苯炔在有机合成化学领域的发展前景进行了展望.

关键词： 锆-苯炔; 金属杂环; 反应性能; 偶联反应

本文引用格式

毛可彬 , 付晓平 , 刘丹 , 李石 , 刘元红 . 锆-苯炔参与的金属杂环的形成及其在有机合成中的应用[J]. 有机化学, 2013 , 33(04) : 780 -791 . DOI: 10.6023/cjoc201211023

Abstract

Zirconium-benzyne complex is an important and highly reactive organometallic species. It can react with unsaturated substrates such as alkenes, alkynes, aldehydes, ketones, nitriles etc. to form metallacyles. A large variety of metallacycles can be constructed by modifying the substitution patterns of the substrates, chemical ratio of reactants, different Cp ligands or reaction conditions and so on. These metallacycles are highly useful for further transformations through the reactions with different electrophiles. This review summarizes the synthetic methods of zirconium-benzyne complexes, reactions of zirconium-benzyne complexes with various unsaturated molecules leading to metallacycles, and the applications of these metallacycles in organic chemistry. An outlook of zirconium-benzyne complexes in organic synthesis is also provided at the end of this review.

Key words： zirconium-benzyne; metallacycle; reactivity; coupling reaction

参考文献

[1] (a) Kitamura, T. Aust. J. Chem. 2010, 63, 987.
(b) Wentrup, C. Aust. J. Chem. 2010, 63, 979.

[2] (a) Wu, Q.; Li, B.; Shi, C.; Chen, Y. Chin. J. Synth. Chem. 2007, 15, 111 (in Chinese).
(仵清春, 李保山, 石常青, 陈彦逍, 合成化学, 2007, 15, 111.)
(b) Xing, Q.; Xu, R.; Zhou, Z.; Pei, W. Basic Organic Chemistry, 2nd ed., Higher Education Press, Beijing, 1994 (in Chinese).
(邢其毅, 徐瑞秋, 周政, 裴伟伟, 基础有机化学(第二版), 高等教育出版社, 北京, 1994.)
(c) Matsumoto, T.; Hosoya, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1991, 32, 6735.
(d) Schlosser, M.; Castagnetti, E. Eur. J. Org. Chem. 2001, 3991.
(e) Caster, K. C.; Keck, C. G.; Walls, R. D. J. Org. Chem. 2001, 66, 2932.
(f) Vagin, S. I.; Frickenschmidt, A.; Kammerer, B.; Hanack, M. Chem. Eur. J. 2007, 13, 985.
(g) Kitamura, T.; Yamane, M. J. Chem. Soc., Chem. Commun. 1995, 983.
(h) Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.

[3] (a) Majoral, J.-P.; Igau, A.; Cadierno, V.; Zablocka, M. Top. Curr. Chem. 2002, 220, 53.
(b) Majoral, J.-P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178～180, 145.
(c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047.
(d) Jones, W. M.; Klosin, J. ChemInform 1998, 29, 1522.

[4] Samuel, E.; Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263.

[5] Clegg, W.; Horsburgh, L.; Lindsaym D. M.; Mulvey, R. E. Acta Crystallogr. 1998, C54, 315.

[6] Erker, G. J. Organomet. Chem. 1977, 134, 189.

[7] Buchwald, S. L.; Watson, B. T. J. Am. Chem. Soc. 1986, 108, 7411.

[8] Buchwald, S. L.; Lucas, E. A.; Dewan, J. C. J. Am. Chem. Soc. 1987, 109, 4396.

[9] Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685.

[10] Tidwell, J. H.; Peat, A. J.; Buchwald, S. L. J. Org. Chem. 1994, 59, 7164.

[11] Tidwell, J. H.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11797.

[12] Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.

[13] Barr, K. J.; Waston, B. T.; Buchwald, S. L. Tetrahedron Lett. 1991, 32, 5465.

[14] (a) Negishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407.
(b) Swanson, D. R.; Nguyen, T.; Noda, Y.; Negishi, E. J. Org. Chem. 1991, 56, 2590.

[15] Rosa, P.; Floch, P. L.; Ricard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417.

[16] Legrand, C.; Meunier, P.; Petersen, J. L.; Tavares, P.; Bodiguel, J.; Gautheron, B.; Dousse, G. Organometallics 1995, 14, 162.

[17] Erker, G.; Kropp, K. J. Am. Chem. Soc. 1979, 101, 3659.

[18] Kropp, K.; Erker, G. Organometallics 1982, 1, 1246.

[19] Zablocka, M.; Cénac, N.; Igau, A.; Donnadieu, B.; Majoral, J. P.; Skowronska, A.; Meunier, P. Organometallics 1996, 15, 5436.

[20] (a) Hanka, L. J.; Dietz, A.; Gerpheide, S. A.; Kuentzel, S. L.; Martin, D. G. J. Antibiot. 1978, 31, 1211.
(b) Chidester, C. G.; Krueger, W. C.; Mizsak, S. A.; Duchamp, D. J.; Martin, D. G. J. Am. Chem. Soc. 1981, 103, 7629.

[21] Tidwell, J. H.; Buchwald, S. L. J. Org. Chem. 1992, 57, 6380.

[22] Wang, C.; Deng, L.; Yan, J.; Wang, H.; Luo, Q.; Zhang, W.; Xi, Z. Chem. Commun. 2009, 4414.

[23] Barluenga, J.; Calleja, J.; Antón, M. J.; álvarez-Rodrigo, L.; Rodríguez, F.; Fananás, F. J. Org. Lett. 2008, 10, 4469.

[24] Ma, X.-B.; Regitz, M. Synthesis 1995, 667.

[25] Miquel, Y.; Igau, A.; Donnadieu, B.; Majoral, J.-P.; Dupuis, L.; Pirio, N.; Meunier, P. Chem. Commun. 1997, 279.

[26] Miquel, Y.; Cadierno, V.; Donnadieu, B.; Igau, A.; Majoral, J.-P. Organometallics 2000, 19, 54.

[27] Cadierno, V.; Igau, A.; Donnadieu, B.; Caminade, A. M.; Majoral, J.-P. Organometallics 1999, 18, 1580.

[28] Cadierno, V.; Zablocka, M.; Donnadieu, B.; Igau, A.; Majoral, J.-P. Organometallics 1999, 18, 1882.

[29] Miquel, Y.; Igau, A.; Donnadieu, B.; Majoral, J.-P.; Pirio, N.; Meunier, P. J. Am. Chem. Soc. 1998, 120, 3504.

[30] Cadierno, V.; Zablocka, M.; Donnadieu, B.; Igau, A.; Majoral, J.-P.; Skowronska, A. Chem. Eur. J. 2000, 6, 345.

[31] Dupuis, L.; Pirio, N.; Meunie, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. 1997, 36, 987.

[32] Mao, S. S. H.; Tilley, T. D. J. Organomet. Chem. 1996, 521, 425.

[33] Duan, Z.; Nakajima, K.; Takahashi, T. Chem. Commun. 2001, 1672.

[34] Zhao, C.; Li, P.; Cao, X.; Xi, Z. Chem. Eur. J. 2002, 8, 4292.

[35] Chen, C.; Xi, C.; Liu, Y.; Hong, X. J. Org. Chem. 2006, 71, 5373.

[36] Bredeau, S.; Delmas, G.; Pirio, N.; Richard, P.; Donnadieu, B.; Meunier, P. Organometallics 2000, 19, 4463.

[37] Bredeau, S.; Ortega, E.; Delmas, G.; Richard, P.; Frohlich, R.; Donnadieu, B.; Kehr, G.; Pirio, N.; Erker, G.; Meunier, P. Organometallics 2009, 28, 181.

[38] Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int. Ed. 2009, 48, 5500.

[39] Fu, X.; Liu, Y.; Li, Y. Organometallics 2010, 29, 3012.

[40] Buchwald, S. L.; Sayers, A.; Watson, B. T.; Dewan, J. C. Tetrahedron Lett. 1987, 28, 3245.

[41] Akai, S.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9119.

[42] Bodlguel, J.; Meunier, P.; Kubicki, M. M.; Richard, P.; Gautheron, B.; Dousse, G.; Lavayssière, H.; Satgé, J. Organometallics 1992, 11, 1423.

[43] Dupuis, L.; Pirio, N.; Meunier, P.; Gautheron, B.; Mahieu, A.; Igau, A.; Majoral, J. P. Bull. Soc. Chim. Fr. 1996, 133, 611.

[44] Rege, F. M. G.; Davis, W. M.; Buchwald, S. L. Organometallics 1995, 14, 4799.

[45] Tavarès, P.; Meunier, P.; Kubicki, M. M.; Gautheron, B.; Dousse, G.; Lavayssière, H.; Satgé, J. Heteroat. Chem. 1993, 4, 383.Mazouz, A.; Meunier, P.; Kubicki, M. M.; Hanquet, B.; Amardeil, R.; Bornet, C.; Zahidi, A. J. Chem. Soc., Dalton Trans. 1997, 1043.
Options
文章导航

/

〈 〉