Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes

doi:10.6023/cjoc201505013

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2119-2124.DOI: 10.6023/cjoc201505013 Previous Articles Next Articles

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芳甲叉双噁唑啉-铜络合物催化三氟甲基丙酮酸酯与吲哚的傅-克烷基化反应研究

殷伯翰, 吴燕华, 麻红利, 马晓东, 傅滨, 刘吉平

中国农业大学理学院北京 100193

收稿日期:2015-05-07 修回日期:2015-06-08 发布日期:2015-06-16
通讯作者: 傅滨, 刘吉平 E-mail:fubinchem@cau.edu.cn
基金资助:
国家自然科学基金(Nos. J1210064, 21172255)资助项目.

Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes

Yin Bohan, Wu Yanhua, Ma hongli, Ma Xiaodong, Fu Bin, Liu Jiping

College of Science, China Agricultural University, Beijing 100193

Received:2015-05-07 Revised:2015-06-08 Published:2015-06-16
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. J1210064, 21172255).

1. Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes.PDF(696KB)

Abstract

This paper reported the reaction of indoles with trifluoromethyl pyruvate catalyzed by heteroaryliden-tethered bis-oxazoline-Cu(II) complex, and the effects of ligand structure, solvent, temperature and different indole substrates on the catalytic reactions were investigated. The results indicate that the reaction furnished high reactivity and moderate to good enantioselectivity, and the substituents on the indole ring have important impact on the reaction. The reaction can afford the indole derivatives with a chiral tertiary carbon center bearing trifluoromethyl substituent in high yields with moderate to good enantioselectivities.

Key words: trifluoromethyl, Friedel-Crafts, indole, bis-oxazoline

Cite this article

Yin Bohan, Wu Yanhua, Ma hongli, Ma Xiaodong, Fu Bin, Liu Jiping. Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes[J]. Chin. J. Org. Chem., 2015, 35(10): 2119-2124.

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[1] (a) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.(b) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)(c) Zhang. K.; Xu, X.-H.; Qing, F. L. Chin. J. Org. Chem. 2015, 35, 556 (in Chinese). (张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
[2] (a) Lv, C.-P.; Shen, Q.-L.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380 (in Chinese). (吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.)(b) Liu, J.-C.; Cui, Z.-P.; He, H.-W. Chin. J. Org. Chem. 2012, 32, 1925 (in Chinese). (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.) (c) Liang, Y.; He, H.-W.; He, H.-F.; Yang, Z.-W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese). (梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.) (d) Xiao, Y.-Y.; Feng, J.; Jiang, Y. G.; Feng, J. Z. Mater. Rev. 2014, 28, 20 (in Chinese). (肖芸芸, 冯坚, 姜勇刚, 冯军宗, 材料导报, 2014, 28, 20.)
[3] (a) Nagib, D. A., Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875. (b) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.(c) Liu, Y.-L.; Shi, T.-D.; Zhou, F.; Zhao, X.-L.; Wang, X.; Zhou, J. Org. Lett. 2011,13,3826.(d) Liu, Y.-L.; Zhou, J. Chem. Commun. 2012,48,1919.(e) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.(f) Liu, Y.-L.; Wang, X.; Zhao, Y.-L.; Zhu, F.; Zeng, X.-P.; Chen, L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Angew. Chem., Int. Ed. 2013, 52, 13735.(g) Gao, J.-R.; Wu, H.; Xiang, B.; Yu, W.-B.; Han, L.; Jia, Y.-X. J. Am. Chem. Soc. 2013, 135, 2983.(h) Yang, X.-Y.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826.(i) Yu, J. -Sh.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L., Zhou, J. Angew. Chem., Int. Ed. 2015, 54, 7381.
[4] (a) Zeng, M.; You, S.-L. Synlett 2010, 1289.(b) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.(c) Shiri, M. Chem. Rev. 2012, 112, 3508.(d) Loh, C. C. J.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 46.(e) Zhang, L.; Zheng, M.-Y.; Zhao, F.; Zhai, Y.; Liu, H. ACS Comb. Sci. 2014, 16, 184.
[5] (a) Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086.(b) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.(c) Hui, Y.-H.; Chen, W.-L.; Wang, W.-T.; Jiang, J.; Cai, Y.-F.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Adv. Synth. Catal. 2010, 352, 3174.(d) Xu, X.-H.; Kusuda, A.; Tokunaga, E.; Shibata, N. Green Chem. 2011, 13, 46.(e) Rueping, M.; Bootwicha, T.; Kambutong, S.; Sugiono, E. Chem. Asian J. 2012, 7, 1195.(f) Han, X.; Ouyang, W.-J.; Liu, B.; Wang, W.; Tien, P.; Wu, Sh. W.; Zhou, H.-B. Org. Biomol. Chem. 2013, 11, 8463.(g) Han, X.; Wu, H.-M.; Wang, W.; Dong, C.; Tien, P.; Wu, S.-W.; Zhou, H.-B. Org. Biomol. Chem. 2014, 12, 8308.
[6] (a) Sun, Y.-J.; Li, N.; Zheng, Z.-B.; Liu, L.; Yu, Y.-B.; Qin, Z.-H.; Fu, B. Adv. Synth. Catal. 2009, 351, 3113.(b) Liu, L.; Zhao, Q.-Y.; Du, F.-P.; Chen, H.-L.; Qin, Z.-H.; Fu, B. Tetrahedron: Asymmetry 2011, 22, 1874.(c) Liu, L.; Ma, H.-L.; Xiao, Y.-M.; Du, F.-P.; Qin, Z.-H.; Li, N.; Fu, B. Chem. Commun. 2012, 48, 9281.(d) Ma, H.-L.; Li, J.-Q.; Sun, L.; Hou, X.-H.; Zhang, Z.-H.; Fu, B. Tetrahedron 2015, 71, 3625.
[7] Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
[8] Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2011, 111, 284.
[9] Crystallographic Data Centre as supplementary publication number CCDC 840559. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk.
[10] Rudnitskaya, A.; Borkin, D. A.; Huynh, K.; Torok, B.; Stieglitz, K. ChemMedChem 2010, 5, 384.
[11] Wolf, C.; Zhang, P. Adv. Synth. Catal. 2011, 353, 760.

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芳甲叉双噁唑啉-铜络合物催化三氟甲基丙酮酸酯与吲哚的傅-克烷基化反应研究

Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes

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