Chinese Journal of Organic Chemistry >
Transition-Metal-Catalyzed Highly Selective Electrophilic Cycloisomerization Reaction of Multi-alkynyl Compounds
Received date: 2014-12-31
Revised date: 2015-02-01
Online published: 2015-02-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21202065, 21462022), and the Natural Science Foundation of Jiangxi Province (No. 20142BAB213004).
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.
Zhu Hui , Yan Bingyu , Cao Yang , Chen Zhiyuan . Transition-Metal-Catalyzed Highly Selective Electrophilic Cycloisomerization Reaction of Multi-alkynyl Compounds[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 509 -521 . DOI: 10.6023/cjoc201412056
[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.
/
〈 |
|
〉 |