Transition-Metal-Catalyzed Highly Selective Electrophilic Cycloisomerization Reaction of Multi-alkynyl Compounds

doi:10.6023/cjoc201412056

Abstract

This article summarized our recent progress in transition-metal-catalyzed highly selective cycloisomerization reactions of 1,5- and/or 1,6-diylol compounds, which selectively provided useful access to polyfunctionalized benzo[a]fluorenol and densely trisubstituted naphthalene derivatives. Based on these results, we have also developed transition-metal-catalyzed tandem cycloisomerization reactions of 1,6-diynl esters or 1,5-diyls, affording a series of methelene benzofulvenes derivatives and trifluoromethanesulfanyl benzofulvenes in chemo- and regio-selective manner. In addition, the factors that may affect the reaction processes were studied, and the possible reaction mechanisms are proposed.

Key words: transition-metal-catalyzed, multi-alkynyl compounds, cycloisomerization, tandem reaction

Cite this article

Zhu Hui, Yan Bingyu, Cao Yang, Chen Zhiyuan. Transition-Metal-Catalyzed Highly Selective Electrophilic Cycloisomerization Reaction of Multi-alkynyl Compounds[J]. Chin. J. Org. Chem., 2015, 35(3): 509-521.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Michelet, V.; Toullec, P. Y.; Genet, J. Angew. Chem., Int. Ed. 2008, 47, 4268.
[2] Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
[3] Luo, Y.; Pan, X.; Yu, X.; Wu, J. Chem. Soc. Rev. 2014, 43, 836.
[4] (a) Schmidbaur, H.; Schier, A. In Science of Synthesis, Vol. 3, Ed.: Olneil, I. A., Thieme, Stuttgart, 2004, p. 691. (b) Gimeno, M. C.; Laguna, A. In Comprehensive Coordination Chemistry II, Vol. 5, Eds.: Constable, E. C.; Dilworth, J. R., Elsevier, Oxford, 2004, p. 911. (c) Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379. (d) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
[5] (a) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208. (b) Sohel, S. M.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269.
[6] Godoi, B.; Schumacher, R.; Zeni, G. Chem. Rev. 2011, 111, 2937.
[7] (a) Chen, Z.; Ye, C.; Zhu, H.; Zeng, X.; Yuan, J. Chem.-Eur. J. 2014, 20, 4237. (b) Ye, C.; Zhu, H.; Chen, Z.; Wu, J. J. Org. Chem. 2014, 79, 8900. (c) Li, Y.; Gao, L.; Zhu, H.; Li, G.; Chen, Z. Org. Biomol. Chem. 2014, 12, 6982. (d) Huang, P.; Chen, Z.; Yang, Q.; Peng, Y. Org. Lett. 2012, 14, 2790. (e) Huang, P.; Yang, Q.; Chen, Z.; Ding, Q.; Xu, J.; Peng, Y. J. Org. Chem. 2012, 77, 8092.
[8] (a) Chen, Z.; Ding, Q.; Yu, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 1692. (b) Chen, Z.; Yu, X.; Su, M.; Wu, J. Adv. Synth. Catal. 2009, 351, 2702.
[9] (a) Chen, Z.; Zeng, M.; Yuan, J.; Yang, Q.; Peng, Y. Org. Lett. 2012, 14, 3588. (b) Chen, Z.; Zeng, M.; Yang, Q.; Peng, Y. CN 102659512, 2012 [Chem. Abstr. 2012, 157, 492411].
[10] Chen, Z.; Jia, X.; Ye, C.; Qiu, G. Y.; Wu, J. Chem.-Asian J. 2014, 9, 126.
[11] Chen, Z.; Jia, X.; Huang, J.; Yuan, J. J. Org. Chem. 2014, 79, 10674.
[12] Xiao, Q.; Zhu, H.; Li, G.; Chen, Z. Adv. Synth. Catal. 2014, 356, 3809.
[13] (a) Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207. (b) Mithani, S.; Weeratunga, G.; Taylor, N. J.; Dmitrienko, G. I. J. Am. Chem. Soc. 1994, 116, 2209.
[14] Gould, S. J.; Melville, C. R. Bioorg. Med. Chem. Lett. 1995, 6, 51.
[15] Gould, S. J.; Melville, C. R.; Cone, M. C.; Chen, J.; Carney, J. R. J. Org. Chem. 1997, 62, 320.
[16] (a) Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 1999, 40, 7701. (b) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. Org. Lett. 2000, 2, 1497. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 2002, 43, 2717. (d) Rodríguez, D.; Quintás, D.; García, A.; Saá, C.; Domínguez, D. Tetrahedron Lett. 2004, 45, 4711.
[17] (a) Liu, L.; Zhang, J.-L. Angew. Chem., Int. Ed. 2009, 48, 6093. (b) Liu, L.; Wei, L.; Zhang, J.-L. Adv. Synth. Catal. 2010, 352, 1920.
[18] (a) Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259. (b) Shi, M.; Horn, M.; Kobashiya, S.; Mayr, H. Chem.-Eur. J. 2009, 15, 8533.
[19] (a) Kitamura, T.; Kobayashi, S.; Taniguchi, H.; Rappoport, Z. J. Org. Chem. 1982, 47, 5003. (b) Chen, X.; Lu, P.; Wang, Y.-G. Chem.-Eur. J. 2011, 17, 8105.
[20] (a) Meyers, A. I.; Willemsen, J. J. Chem. Commun. 1997, 1573. (b) Kometani, T.; Takeuchi, Y.; Yoshii, E. J. Org. Chem. 1983, 48, 2630. (c) Lester, W. Annu. Rev. Microbiol.1972, 26, 85. (d) Rinehart, K. L.; Jr. Acc. Chem. Res. 1972, 5, 57. (e) Laatsch, H. Angew. Chem., Int. Ed. 1994, 106, 438.
[21] Fu, G.; Yoda, T.; Kasatani, K.; Okamoto, H.; Takenaka, S. Jpn. J. Appl. Phys. 2005, 44, 3945.
[22] Niu, R.-M.; Zhu, X.-R.; Sun, Z.-R. Acta Opt. Sinica 2003, 23, 18 (in Chinese). (牛瑞民, 朱小蓉, 孙真荣, 光学学报, 2003, 23, 18.)
[23] Wang, L.; Zhu, H.; Lu, L.; Yang, F.; Liu, X.-Y; Liang, Y.-M. Org. Lett. 2012, 14, 1990.
[24] (a) Lavery, C. B.; McDonald, R.; Stradiotto, M. Chem. Commun. 2012, 48, 7277. (b) Tang, Z.; Hu, Q.-S. Adv. Synth. Catal. 2006, 348, 846. (c) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
[25] Asao, N. Synlett 2006, 1645.
[26] (a) Wang, Z.-G.; Chen, L. -Q.; Chen, J.-B.; Zheng, J. F.; Gao, W.-W.; Zeng, Z.-P.; Zhou, H.; Zhang, X.-K.; Huang, P.-Q.; Su, Y. Eur. J. Med. Chem. 2013, 62, 632. (b) Karaguni, I. M.; Glusenkamp, K. H.; Langerak, A.; Geisen, C.; Ullrich, V.; Winde, G.; Moroy, T.; Muller, O. Bioorg. Med. Chem. Lett. 2002, 12, 709. (c) Clegg, N. J.; Paruthiyil, S.; Leitman, D. C.; Scanlan, T. S. J. Med. Chem. 2005, 48, 5989. (d) Halder, S.; Satyam, A. Tetrahedron Lett. 2011, 52, 1179. (e) Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723.
[27] (a) Ye, L.; Wang, Y.; Aue, D.; Zhang, L. J. Am. Chem. Soc. 2012, 134, 31. (b) Hashmi, A.; Braun, I.; Nosel, P.; Schadlich, J.; Wieteck, M.; Rudolph, M.; Rominger, F. Angew. Chem. Int. Ed. 2012, 51, 4456. (c) Li, C.; Zeng, Y.; Wang, J. Tetrahedron Lett. 2009, 50, 2956. (d) Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 5406. (e) Ye, S.; Wu, J. Org. Lett. 2011, 13, 5980. (f) Hwang, J. H.; Jung, Y. H.; Hong, Y. Y.; Jeon, S. L.; Jeong, I. H. J. Fluorine Chem. 2011, 132, 1227. (g) Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2154. (h) Lee, P. S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 17283. (i) Schmittel, M.; Vavilala, C. J. Org. Chem. 2005, 70, 4865. (j) Bucher, G.; Mahajan, A. A.; Schmittel, M. J. Org. Chem. 2008, 73, 8815.
[28] (a) Zhang, G.; Catalano, V. J.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 11358. (b) Cho, E. J. Chem. Eur. J. 2012, 18, 4495.
[29] (a) Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244. (b) Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024. (c) Fürstner, A.; Assa, C. J. Am. Chem. Soc. 2006, 128, 6306. (d) Hsu, Y.; Ting, C.; Liu, R.-S. J. Am. Chem. Soc. 2009, 131, 2090. (e) Lu, L.; Liu, X.; Shu, X.; Yang, K.; Ji, K.; Liang, Y. J. Org. Chem. 2009, 74, 474.
[30] CCDC1040967 (24a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data_request/cif.
[31] Unpublished results, manuscript under preparation.
[32] (a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. (b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
[33] (a) Curtis-Prior, P.; Prouteau, M. Int. J. Obes. 1983, 7, 575. (b) Colliot, F.; Kukorowski, K.; Hawkins, D.; Roberts, D. Brighton Crop Prot. Conf. 1992, 1, 29. (c) Hamon, N.; Shaw, R.; Yang, H. Proc.-Beltwide Cotton Conf. 1996, 2, 759. (d) Swingle, K. F.; Harrington, J. K.; Hamilton, R.; Kvam, D. C. Arch. Int. Phamacodyn. Ther. 1971, 192, 16.
[34] (a) Chen, C.; Xie, Y.; Chu, L.; Wang, R.; Zhang, X.; Qing, F.-L. Angew. Chem., Int. Ed. 2012, 51, 2492. (b) Tyrra, W.; Naumann, D.; Hoge, B.; Yaguploskii, Y. L. J. Fluorine Chem. 2003, 119, 101. (c) Man, E. H.; Coffmann, D. D.; Muetterties, E. L. J. Am. Chem. Soc. 1959, 81, 3575. (d) Adams, D. J.; Clark, J. H. J. Org. Chem. 2000, 65, 1456. (e) Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312.
[35] (a) Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 12860. (b) Yang, Y.; Jiang, X.; Qing, F.-L. J. Org. Chem. 2012, 77, 7538. (c) Bootwicha, T.; Liu, X.; Pluta, R.; Atodiresei, I.; Rueping, M. Angew. Chem., Int. Ed. 2013, 52, 12856. (d) Ferry, A.; Billard, T. B.; Langlois, R.; Bacqué, E. Angew. Chem. Int. Ed. 2009, 48, 8551.
[36] Xiao, Q.; Sheng, J.; Chen, Z.; Wu, J. Chem. Commun. 2013, 49, 8647.
[37] Ferry, A.; Billard, T.; Langlois, R.; Bacqué. E. Angew. Chem., Int. Ed. 2009, 48, 8551.

过渡金属催化的多炔基化合物高选择性亲电环异构化反应研究