钯催化的串联反应构建苯并五元杂环的研究进展
收稿日期: 2015-08-10
修回日期: 2015-11-02
网络出版日期: 2015-11-06
基金资助
四川省科技厅应用基础项目基金(No. 2012JY0118)和四川农业大学资助项目.
Progress in Palladium-Catalyzed Tandem Reaction of Constructing Benzo-Five-Membered Heterocycles
Received date: 2015-08-10
Revised date: 2015-11-02
Online published: 2015-11-06
Supported by
Project supported by the Science & Technology Department of Sichuan Province (No. 2012JY0118) and the Sichuan Agricultural University.
丁刚 , 王泽宇 , 殷中琼 , 乐贵洲 . 钯催化的串联反应构建苯并五元杂环的研究进展[J]. 有机化学, 2016 , 36(1) : 43 -59 . DOI: 10.6023/cjoc201508012
The benzo-five-membered heterocycles existed extensively in many important natural products and also showed excellent bioactivites. Therefore, organic chemists around the world made efforts to develop the highly efficient methods of constructing these heterocycles. Recently, the syntheses of them via transition metal-catalyzed tandem reaction, especially palladium-catalyzed reaction, have been reported widely. This review emphasizes on the palladium-catalyzed tandem reaction of the formation of benzo-five-membered heterocycles and their derivatives reported since 2000.
Key words： heterocycle; tandem reaction; palladium catalyst; synthesis
[1] Luize, P. S.; Ueda-Nakamura, T.; Filho, B. P. D.; Cortez, D. A. G.; Nakamura, C. V. Biol. Pharm. Bull. 2006, 29, 2126.
[2] Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.
[3] Li, H.; Ding, C.; Xu, B.; Hou, X. Acta Chim. Sinica 2014, 72, 765 (in Chinese). (李浩, 丁昌华, 许斌, 侯雪龙, 化学学报, 2014, 72, 765.)
[4] Liu, J.; Zhu, Q.; Du, J.; Zhang, X. Chin. J. Org. Chem. 2015, 35, 15 (in Chinese). (刘杰, 朱庆仁, 杜鹃, 张袖丽, 有机化学, 2015, 35, 15.)
[5] Ni, C.; Shen, A.; Cao, Y.; Ye, X. Chin. J. Org. Chem. 2014, 34, 278 (in Chinese). (倪晨, 沈安, 曹育才, 叶晓峰, 有机化学, 2014, 34, 278.)
[6] Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90 (in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
[7] Xiao, Y.; Pan, Q.; Zhang, X. Acta Chim. Sinica 2015, 73, 383 (in Chinese). (肖玉兰, 潘强, 张新刚, 化学学报, 2015, 73, 383.)
[8] Zhang, J.; Lu, Q.; Liu, C.; Lei, A. Chin. J. Org. Chem. 2015, 35, 743 (in Chinese). (张剑, 陆庆全, 刘超, 雷爱文, 有机化学, 2015, 35, 743.)
[9] Zhang, Y.; Feng, B. Chin. J. Org. Chem. 2014, 34, 2406 (in Chinese). (张艳, 冯柏年, 有机化学, 2014, 34, 2406.)
[10] Bai, D.; Li, C.; Li, J.; Jia, X. Chin. J. Org. Chem. 2012, 32, 994 (in Chinese). (白东虎, 李春举, 李健, 贾学顺, 有机化学, 2012, 32, 994.)
[11] Fang, S.; Lü, M.; Long, Y.; Yang, D. Chin. J. Org. Chem. 2011, 31, 1573 (in Chinese). (方晒, 吕梅香, 龙玉华, 杨定乔, 有机化学, 2011, 31, 1573.)
[12] Tang, S.; Liang, Y.; Liu, W.-J.; Li, J.-H. Chin. J. Org. Chem. 2004, 24, 1133 (in Chinese). (唐石, 梁云, 林文杰, 李金恒, 有机化学, 2004, 24, 1133.)
[13] Wang, N. Chin. J. Org. Chem. 2011, 31, 1319 (in Chinese). (王乃兴, 有机化学, 2011, 31, 1319.)
[14] Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
[15] Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
[16] Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428 (in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
[17] Sheng, R.-L.; Tang, S.; Zhou, D.; Li, Z.-H.; Fu, M.-J.; Jie, L.; Li, S.-H. Synthesis 2015, 47, 1567.
[18] Gansauer, A.; Hildebrandt, S.; Michelmann, A.; Dahmen, T.; von Laufenberg, D.; Kube, C.; Fianu, G. D.; Flowers, R. A. Angew. Chem., Int. Ed. 2015, 54, 7003.
[19] Wei, X.-H.; Wu, Q.-X.; Yang, S.-D. Synlett 2015, 26, 1417.
[20] Fu, W.; Xu, F.; Fu, Y.; Zhu, M.; Yu, J.; Xu, C.; Zou, D. J. Org. Chem. 2013, 78, 12202.
[21] Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803.
[22] Grigg, R.; Sridharan, V. Tetrahedron 1999, 576, 65.
[23] Wei, H.-L. Ph.D. Dissertation, Lanzhou University, Lanzhou, 2010 (in Chinese). (韦海龙, 博士论文, 兰州大学, 兰州, 2010.)
[24] Shen, J.; Cheng, G.; Cui, X. Prog. Chem. 2012, 24, 1324 (in Chinese). (沈金海, 程国林, 崔秀灵, 化学进展, 2012, 24, 1324.)
[25] Li, J.-H.; Song, R.-J.; Liu, Y.; Xie, Y.-X. Synthesis 2015, 47, 1195.
[26] Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilsona, D.; Redpathb, J. Tetrahedron 2000, 56, 7525.
[27] Casaschi, A.; Grigg, R.; Sansano, J. M. Tetrahedron 2000, 56, 7553.
[28] Jeffery, T. Tetrahedron 1996, 52, 10113.
[29] Casaschi, A.; Grigg, R.; Sansano, J. M.; Wilsona, D.; Redpathb, J. Tetrahedron 2000, 56, 7541.
[30] Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Sridharan, V.; Suganthan, S. Tetrahedron 2001, 57, 10335.
[31] Anwar, U.; Fielding, M. R.; Grigg, R.; Sridharan, V.; Urch, C. J. J. Org. Chem. 2006, 691, 1476.
[32] Szlosek-Pinaud, M.; Diaz, P.; Martinez, J.; Lamaty, F. Tetrahedron 2007, 63, 3340.
[33] Grigg, R.; Mariani, E.; Sridharan, V. Tetrahedron Lett. 2001, 42, 8677.
[34] Szlosek-Pinaud, M.; Diaz, P.; Martinez, J.; Lamaty, F. Tetrahedron Lett. 2003, 44, 8657.
[35] Yanada, R.; Obika, S.; Inokuma, T.; Yanada, K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem. 2005, 70, 6972.
[36] Packer, G.; Lepre, K.; Kankanala, J.; Sridharan, V. RSC Adv. 2014, 4, 3457.
[37] Liu, P.; Huang, L.; Lu, Y.; Dilmeghani, M.; Baum, J.; Xiang, T.; Adams, J.; Tasker, A.; Larsen, R.; Faul, M. M. Tetrahedron Lett. 2007, 48, 2307.
[38] Kim, H. S.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 3154.
[39] Day, J.; Frederickson, M.; Hogg, C.; Johnson, C.; Meek, A.; Northern, J.; Reader, M.; Reid, G. Synlett 2015, 26, 2570.
[40] Grigg, R.; Savic, V.; Sridharan, V.; Terrier, C. Tetrahedron 2002, 58, 8613.
[41] Jaegli, S.; Erb, W.; Retailleau, P.; Vors, J. P.; Neuville, L.; Zhu, J. Chem. Eur. J.2010, 16, 5863.
[42] Seashore-Ludlow, B.; Somfai, P. Org. Lett. 2010, 12, 3732.
[43] Liu, X.; Li, B.; Gu, Z. J. Org. Chem.2015, 80, 7547.
[44] René, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560.
[45] Kim, H. S.; Gowrisankar, S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3858.
[46] Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711.
[47] Piou, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2012, 51, 11561.
[48] Piou, T.; Neuville, L.; Zhu, J. Org. Lett. 2012, 14, 3760.
[49] Piou, T.; Bunescu, A.; Wang, Q.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 12385.
[50] Bunescu, A.; Piou, T.; Wang, Q.; Zhu, J. Org. Lett.2015, 17, 334.
[51] Wang, W.; Zhou, R.; Jiang, Z.-J.; Wang, X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Eur. J. Org. Chem.2015, 2015, 2579.
[52] Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Eur. Chem. J.2007, 13, 961.
[53] Lee, H.-S.; Kim, K.-H.; Lim, J.-W.; Kim, J.-N. Bull. Korean Chem. Soc. 2011, 32, 1083.
[54] Kamisaki, H.; Yasui, Y.; Takemoto, Y. Tetrahedron Lett. 2009, 50, 2589.
[55] Hande, S. M.; Nakajima, M.; Kamisaki, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2011, 13, 1828.
[56] Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 1778.
[57] Liu, X.; Ma, X.; Huang, Y.; Gu, Z. Org. Lett.2013, 15, 4814.
[58] Jiang, T. S.; Tang, R. Y.; Zhang, X. G.; Li, X. H.; Li, J. H. J. Org. Chem. 2009, 74, 8834.
[59] Jaegli, S.; Dufour, J.; Wei, H. L.; Piou, T.; Duan, X. H.; Vors, J. P.; Neuville, L.; Zhu, J. Org. Lett. 2010, 12, 4498.
[60] Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578.
[61] Mu, X.; Wu, T.; Wang, H. Y.; Guo, Y. L.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878.
[62] Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüßeler, T.; Yamamoto, Y. Angew. Chem., Int. Ed.2005, 44, 7718.
[63] Miura, T.; Toyoshima, T.; Ito, Y.; Murakami, M. Chem. Lett. 2009, 38, 1174.
[64] Miura, T.; Toyoshima, T.; Takahashi, Y.; Murakami, M. Org. Lett. 2009, 11, 2141.
[65] Toyoshima, T.; Mikano, Y.; Miura, T.; Murakami, M. Org. Lett. 2010, 12, 4584.
[66] Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906.
[67] Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1208.
[68] Thansandote, P.; Hulcoop, D. G.; Langer, M.; Lautens, M. J. Org. Chem.2009, 74, 1673.
[69] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Sferrazza, A. Org. Biomol. Chem. 2011, 9, 1727.
[70] Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagne, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066.
[71] Agasti, S.; Maity, S.; Szabo, K. J.; Maiti, D. Adv. Synth. Catal. 2015, 357, 2331.
[72] Pinto, A.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed.2007, 46, 3291.
[73] Tang, S.; Peng, P.; Pi, S. F.; Liang, Y.; Wang, N. X.; Li, J. H. Org. Lett. 2008, 10, 1179.
[74] Tang, S.; Peng, P.; Wang, Z.-Q.; Tang, B.-X.; Deng, C.-L.; Li, J.-H.; Zhong, P.; Wang, N.-X. Org. Lett. 2008, 10, 1875.
[75] An, G.; Zhou, W.; Zhang, G.; Sun, H.; Han, J.; Pan, Y. Org. Lett. 2010, 12, 4482.
[76] Wang, J. Y.; Su, Y. M.; Yin, F.; Bao, Y.; Zhang, X.; Xu, Y. M.; Wang, X. S. Chem. Commun. 2014, 50, 4108.
[77] Nicolai, S.; Erard, S.; Gonzalez, D. F.; Waser, J. Org. Lett. 2010, 12, 384.
[78] Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130.
[79] Yip, K. T.; Zhu, N. Y.; Yang, D. Org. Lett. 2009, 11, 1911.
[80] He, W.; Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 5626.
[81] Du, W.; Gu, Q.; Li, Z.; Yang, D. J. Am. Chem. Soc. 2015, 137, 1130.
[82] Mariampillai, B.; Alberico, D.; Bidau, V.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 14436.
[83] Rudolph, A.; Rackelmann, N.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 289.
[84] Wu, X. X.; Zhou, P. X.; Wang, L. J.; Xu, P. F.; Liang, Y. M. Chem. Commun. 2014, 50, 3882.
[85] Thansandote, P.; Raemy, M.; Rudolph, A.; Lautens, M. Org. Lett. 2007, 9, 5255.
[86] Muñiz, K. J. Am. Chem. Soc. 2007, 129, 14543.
[87] Ying, A.-G.; Ye, W.-D.; Liu, L.; Wu, G.-F.; Chen, X.-Z.; Qian, S.; Zhang, Q.-P. Chin. J. Org. Chem. 2008, 28, 2081 (in Chinese). (应安国, 叶伟东, 刘泺, 吴国峰, 陈新志, 钱胜, 张秋萍, 有机化学, 2008, 28, 2081.)
[88] John, J.; Indu, U.; Suresh, E.; Radhakrishnan, K. V. J. Am. Chem. Soc.2009, 131, 5402.
[89] Prakash, P.; Jijy, E.; Preethanuj, P.; Pihko, P. M.; Sarath Chand, S.; Radhakrishnan, K. V. Chem. Eur. J. 2013, 19, 10473.
[90] Chand, S. S.; Jijy, E.; Prakash, P.; Szymoniak, J.; Preethanuj, P.; Dhanya, B. P.; Radhakrishnan, K. V. Org. Lett. 2013, 15, 3338.
[91] Ramirez, T. A.; Wang, Q.; Zhu, Y.; Zheng, H.; Peng, X.; Cornwall, R. G.; Shi, Y. Org. Lett. 2013, 15, 4210.
[92] Zheng, H.; Zhu, Y.; Shi, Y. Angew. Chem., Int. Ed. 2014, 53, 11280.
[93] Campbell, C. D.; Greenaway, R. L.; Holton, O. T.; Chapman, H. A.; Anderson, E. A. Chem. Commun. 2014, 50, 5187.
[94] Senadi, G. C.; Hu, W. P.; Boominathan, S. S.; Wang, J. J. Chem. Eur. J. 2015, 21, 998.
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