SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2009 - 2017

DOI: https://doi.org/10.6023/cjoc201207034

ACCOUNT

Intramolecular Hydrogen Bonding-Promoted Formation of Macrocycles: Dynamical and Thermodynamic Control Approaches

  • Zhang Danwei ,
  • Li Zhanting
Expand
  • Department of Chemistry, Fudan University, Shanghai 200433

Received date: 2012-07-24

  Revised date: 2012-08-28

  Online published: 2012-09-04

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20974118, 21172042).

Fold

Abstract

Hydrogen bonding-induced aromatic amide oligomers may adopt folded, helical, extended or zigzag conformations. This feature of structural preorganization can be utilized to promote the formation of macrocycles. When reactive groups are introduced at the ends of the aromatic amide backbones, the preorganization of the backbones may induce them to adopt discrete required spatial orientations. When macrocyclization concerns the formation of irreversible covalent, carbon-metal and coordination bonds, preorganization may facilitate the formation of specifically designed macrocycles. When macrocyclization involves the formation of reversible covalent bonds such as imine and hydrazone, rationally designed macrocycles may be produced in high or even quantitative yields after the reactions achieve equilibrium and are controlled thermodynamically.

Key words： hydrogen bonding; macrocycle; aromatic amide; imine; dynamically controlled reaction; thermodynamically controlled reaction

Cite this article

Zhang Danwei , Li Zhanting . Intramolecular Hydrogen Bonding-Promoted Formation of Macrocycles: Dynamical and Thermodynamic Control Approaches[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2009 -2017 . DOI: 10.6023/cjoc201207034

References

[1] Gale, P. A.; Steed, J. W. Supramolecular Chemistry: From Molecules to Nanomaterials, Wiley-VCH, Meinheim, 2012.

[2] Dietrich, B.; Lehn, J. M.; Sauvage, J. P.; Blanzat, J. Tetrahedron 1973, 29, 1629.

[3] Rossa. L.: Vogtle, F. Top. Curr. Chem. 1983, 113, 1.

[4] Gokel, G. W.; Cram, D. J.; Liotta, C. L.; Harris, H. P.; Cook, F. L. Org. Synth. 1988, 6, 301.

[5] Gerbeleu, N. V.; Arion, V. B.; Burgess, J. Template Synthesis of Macrocyclic Compounds, Wiley-VCH, Weinheim, 1999.

[6] Diederich, F.; Stang, P. J. Templated Organic Synthesis, Wiley-VCH, Weinheim, 2000.

[7] Reinhoudt, D. N.; Dijkstra, P. J. Pure Appl. Chem. 1988, 60, 477.

[8] Cram, D. J.; Cram, J. M. Container Molecules and Their Guests, The Royal Society of Chemistry, Cambridge, 1994, p. 39.

[9] Wang, M.-X. Acc. Chem. Res. 2012, 45, 182.

[10] Chen, C.-F. Chem. Commun. 2011, 47, 1674.

[11] Zhang, J. Q.; Jia, C. Y. Chin. J. Org. Chem. 2010, 30, 1142 (in Chinese).
(张家强, 贾春阳, 有机化学 2010, 30, 1142.)

[12] Han, Y.-F.; Jia, W.-G.; Yu, W.-B.; Jin, G.-X. Chem. Soc. Rev. 2009, 38, 3419.

[13] Cheng, X.-H.; Ju, X.-P.; Hoeger, S. Chin. J. Org. Chem. 2006, 26, 733 (in Chinese).
(程晓红, 鞠秀萍, 有机化学, 2006, 26, 733.)

[14] Diederich, F.; Stang, P. J.; Tykwinski, R. R. Modern Supramolecular Chemistry Strategies for Macrocycle Synthesis, Wiley-VCH, Weinheim, 2008.

[15] Zhao, X.; Li, Z.-T. Chem. Commun. 2010, 46, 1601.

[16] Li, Z.-T.; Hou, J.-L.; Li, C. Acc. Chem. Res. 2008, 41, 1343.

[17] Gong, B. Acc. Chem. Res. 2008, 41, 1376.

[18] Reek, J. N. H.; Otto, S. Dynamic Combinatorial Chemistry, John Wiley & Sons, Hoboken, 2010.

[19] Mastalerz, M. Angew. Chem., Int. Ed. 2010, 49, 5042.

[20] Hecht, S.; Huc, I. Foldamers: Structure, Properties and Applications, Wiley-VCH, Weinheim, 2007.

[21] Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.

[22] Gong, B. Chem. Eur. J. 2001, 7, 4336.

[23] Huc, I. Eur. J. Org. Chem. 2004, 17.

[24] Guichard, G.; Huc, I. Chem. Commun. 2011, 47, 5933.

[25] Gan, Q.; Wang, Y.; Jiang, H. Curr. Org. Chem. 2011, 15, 1293.

[26] Wang, Y.; Gan, Q.; Jiang, H. Chem. Res. Chin. Univ. 2011, 32, 1928.

[27] Prabhakaran, P.; Priya, G.; Sanjayan, G. J. Angew. Chem., Int. Ed. 2012, 51, 4006.

[28] Li, Z.-T.; Zhang, K.-D.; Shi, Z.-M.; Wang, L.; Zhou, C.; Lu, B.-Y. Pure Appl. Chem. 2012, 84, 965.

[29] Zhu, Y.-Y.; Wang, G.-T.; Li, Z.-T. Curr. Org. Chem. 2011, 15, 1266.

[30] Li, Z.-T. Prog. Chem. 2011, 23, 1 (in Chinese).
(黎占亭, 化学进展, 2011, 23, 1.)

[31] Li, C.-Z.; Jiang, X.-K.; Li, Z.-T.; Gao, X.; Wang, Q.-R. Chin. J. Org. Chem. 2007, 27, 188 (in Chinese).
(李昌治, 蒋锡夔, 黎占亭, 高翔, 王全瑞, 有机化学, 2007, 27, 188.)

[32] Li, Z.-T.; Hou, J.-L.; Li, C.; Yi, H.-P. Chem. Asian J. 2006, 1, 766.

[33] Zhang, D.-W.; Zhao, X.; Hou, J.-L.; Li, Z.-T. Chem. Rev. 2012, 112, 5271.

[34] Wu, Z.-Q.; Jiang, X.-K.; Zhu, S.-Z.; Li, Z.-T. Org. Lett. 2004, 6, 229.

[35] Zhu, J.; Wang, X.-Z.; Chen, Y.-Q.; Jiang, X.-K.; Chen, X.-Z.; Li, Z.-T. J. Org. Chem. 2004, 69, 6221.

[36] Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2006, 128, 12307.

[37] Hou, J.-L.; Shao, X.-B.; Chen, G.-J.; Zhou, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2004, 126, 12386.

[38] Wu, Z.-Q.; Shao, X.-B.; Li, C.; Hou, J.-L.; Wang, K.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2005, 127, 17460.

[39] Li, C.; Ren, S.-F.; Hou, J.-L.; Yi, H.-P.; Zhu, S.-Z.; Jiang, X.-K.; Li, Z.-T. Angew. Chem., Int. Ed. 2005, 44, 5725.

[40] Hou, J.-L.; Yi, H.-P.; Shao, X.-B.; Li, C.; Wu, Z.-Q.; Jiang, X.-K.; Wu, L.-Z.; Tung, C.-H.; Li, Z.-T. Angew. Chem., Int. Ed. 2006, 45, 796.

[41] Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2006, 128, 12307.

[42] Li, C.; Wang, G.-T.; Yi, H.-P.; Jiang, X.-K.; Li, Z.-T.; Wang, R.-X. Org. Lett. 2007, 9, 1797.

[43] Cai, W.; Wang, G.-T.; Xu, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2008, 130, 6936.

[44] Xu, X.-N.; Wang, L.; Li, Z.-T. Chem. Commun. 2009, 6634.

[45] Cai, W.; Wang, G.-T.; Du, P.; Wang, R.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2008, 130, 13450.

[46] Wang, L.; Xiao, Z.-Y.; Hou, J.-L.; Wang, G.-T.; Jiang, X.-K.; Li, Z.-T. Tetrahedron 2009, 65, 10544.

[47] You, L.-Y.; Jiang, X.-K.; Li, Z.-T. Tetrahedron 2009, 65, 9494.

[48] X.-Z.-Y.; Hou, J.-L.; Jiang, X.-K.; Li, Z.-T.; Ma, Z. Tetrahedron 2009, 65, 10182.

[49] Wang, G.-T.; Zhao, X.; Li, Z.-T. Tetrahedron 2011, 67, 48.

[50] Shi, Z.-M.; Huang, J.; Ma, Z.; Zhao, X.; Guan, Z.; Li, Z.-T. Macromolecules 2010, 43, 6185.

[51] Zhang, K.-D.; Zhao, X.; Wang, G.-T.; Liu, Y.; Zhang, Y.; Lu, H.-J.; Jiang, X.-K.; Li, Z.-T. Angew. Chem., Int. Ed. 2011, 50, 9866.

[52] Zhang, K.-D.; Zhao, X.; Wang, G.-T.; Liu, Y.; Zhang, Y.; Lu, H.-J.; Jiang, X.-K.; Li, Z.-T. Tetrahedron 2012, 68, 4517.

[53] Zhu, J.; Wang, X.-Z.; Chen, Y.-Q.; Jiang, X.-K.; Chen, X.-Z.; Li, Z.-T. J. Org. Chem. 2004, 69, 6221.

[54] Chen, Y.-Q.; Wang, X.-Z.; Shao, X.-B.; Hou, J.-L.; Chen, X.-Z.; Jiang, X.-K.; Li, Z.-T. Tetrahedron 2004, 60, 10253.

[55] Wu, Z.-Q.; Jiang, X.-K.; Li, Z.-T. Tetrahedron Lett. 2005, 46, 8067.

[56] Zhu, Y.-Y.; Wang, G.-T.; Li, Z.-T. Org. Biomol. Chem. 2009, 7, 3243.

[57] Kim, Y. H.; Calabrese, J.; McEwen, C. J. Am. Chem. Soc. 1996, 118, 1545.

[58] Choi, K.; Hamilton, A. D. J. Am. Chem. Soc. 2003, 125, 10241.

[59] Kang, S. W.; Gothard, C. M.; Maitra, S.; Atiatul, W.; Nowick, J. S. J. Am. Chem. Soc. 2007, 129, 1486.

[60] Yuan, L.; Feng, W.; Yamato, K.; Sanford, A. R.; Xu, D.; Guo, H.; Gong, B. J. Am. Chem. Soc. 2004, 126, 11120.

[61] Yang, L.; Zhong, L.; Yamato, K.; Zhang, X.; Feng, W.; Deng, P.; Yuan, L.; Zeng, X. C.; Gong, B. New J. Chem. 2009, 33, 729.

[62] Feng, W.; Yamato, K.; Yang, L.; Ferguson, J. S.; Zhong, L.; Zou, S.; Yuan, L.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2009, 131, 2629.

[63] Yang, Y.; Feng, W.; Hu, J.; Zou, S.; Gao, R.; Yamato, K.; Kline, M.; Cai, Z.; Gao, Y.; Wang, Y.; Li, Y.; Yang, Y.; Yuan, L.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2011, 133, 18590.

[64] Jiang, H.; Léger, J.-M.; Guionneau, P.; Huc, I. Org. Lett. 2004, 6, 2985.

[65] Li, F.; Gan, Q.; Xue, L.; Wang, Z.-M.; Jiang, H. Tetrahedron Lett. 2009, 50, 2367.

[66] Qin, B.; Chen, X.; Fang, X.; Shu, Y.; Yip, Y. K.; Yan, Y.; Pan, S.; Ong, W. Q.; Ren, C.; Su, H.; Zeng, H. Org. Lett. 2008, 10, 5127.

[67] Qin, B.; Sun, C.; Liu, Y.; Shen, J.; Ye, R.; Zhu, J.; Duan, X.-F.; Zeng, H. Org. Lett. 2011, 13, 2270.

[68] Du, Z.; Ren, C.; Ye, R.; Shen, J.; Maurizot, V.; Lu, Y.; Wang, J.; Zeng, H. Chem. Commun. 2011, 47, 12488.

[69] Zhu, Y.-Y.; Li, C.; Li, G.-Y.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2008, 73, 1745.

[70] Lin, J.-B.; Xu, X.-N.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2008, 73, 9403.

[71] Lin, J.; Wu, J.; Jiang, X.; Li, Z. Chin. J. Chem. 2009, 27, 117.

[72] Xu, X.-N.; Wang, L.; Lin, J.-B.; Wang, G.-T.; Jiang, X.-K.; Li, Z.-T. Chem. Eur. J. 2009, 15, 5763.

[73] Lu, B.-Y.; Sun, G.-J.; Lin, J.-B.; Jiang, X.-K.; Zhao, X.; Li, Z.-T. Tetrahedron Lett. 2010, 51, 3830.

[74] Xu, X.-N.; Wang, L.; Zhao, X.; Li, Z.-T. Chem. Res. Chin. Univ. 2011, 32, 2162.

[75] Xu, X.-N.; Wang, L.; Li, Z.-T. Chem. Commun. 2009, 6634.

[76] Wang, L.; Wang, G.-T.; Zhao, X.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2011, 76, 3531.

[77] Zou, S.; He, L.; Zhang, J.; He, Y.; Yuan, L.; Wu, L.; Luo, J.; Wang, Y.; Feng, W. Org. Lett. 2012, 14, 3584.

[78] Helsel, A. J.; Brown, A. L.; Yamato, K.; Feng, W.; Yuan, L.; Clements, A. J.; Harding, S. V.; Szabo, G.; Shao, Z.; Gong, B. J. Am. Chem. Soc. 2008, 130, 15784.
Options
Outlines

/

〈 〉