Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes

doi:10.6023/cjoc201702031

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1278-1283.DOI: 10.6023/cjoc201702031 Previous Articles Next Articles

Notes

钯/对甲苯磺酸催化烯丙基苯异构化合成β-甲基苯乙烯衍生物的方法研究（英文）

乌拉·阿齐兹, 张胜, 包明

大连理工大学精细化工国家重点实验室大连 116023

收稿日期:2017-02-21 修回日期:2017-04-13 发布日期:2017-04-27
通讯作者: 张胜 E-mail:shengzhang@dlut.edu.cn
基金资助:
国家自然科学基金（No.21602026）、中国博士后科学基金（No.2016M590226）资助项目.

Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes

Ullah Aziz, Zhang Sheng, Bao Ming

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023

Received:2017-02-21 Revised:2017-04-13 Published:2017-04-27
Contact: 10.6023/cjoc201702031 E-mail:shengzhang@dlut.edu.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (No. 21602026) and the China Postdoctoral Science Foundation (No. 2016M590226).

1. Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes.PDF(2296KB)

Abstract

Convenient and efficient protocol for isomerization of allylbenzenes into corresponding β-methylstyrenes has been developed. Different acids, solvents and catalysts have been investigated. Pd(TFA)₂ and TsOH·H₂O as catalysts in dichloromethane at room temperature under air for 12 h were selected as standard conditions for exploring the substrate scope. Allylbenzenes containing electron-donating groups and electron-withdrawing groups were working under the optimized condition, and β-methylstyrene products were obtained in the yields of 65%～90%. The reaction mechanism was proposed according to the deuterated experiment.

Key words: isomerization, allylbenzene, β-methylstyrene, palladium-catalyzed

Cite this article

Ullah Aziz, Zhang Sheng, Bao Ming. Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes[J]. Chin. J. Org. Chem., 2017, 37(5): 1278-1283.

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[1] (a) Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716.
(b) Gross, P. J.; Brase, S. Chem. Eur. J. 2010, 16, 12660.
(c) Gross, P. J.; Furche, F.; Nieger, M.; Brase, S. Chem. Commun. 2010, 46, 9215.
(d) Kwon, Y.-J.; Sohn, M.-J.; Zheng, C.-J.; Kim, W.-G. Org. Lett. 2007, 9, 2449.
[2] (a) Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2003, 44, 1187.
(b) Lantaño, B.; Aguirre, J. M.; Ugliarolo, E. A.; Benegas, M. L.; Moltrasio, G. Y. Tetrahedron 2008, 64, 4090.
(c) Mondal, P.; Thander, L.; Chattopadhyay, S. K. Tetrahedron Lett. 2012, 53, 1328.
(d) Seijas, J. A.; Vázquez-Tato, M. P.; Entenza, C.; Montserrat Martínez, M.; Ònega, M. G.; Veiga, S. Tetrahedron Lett. 1998, 39, 5073.
[3] (a) Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119.
(b) Gooβen, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2004, 43, 1095.
[4] Jeffery, T. Tetrahedron Lett. 2000, 41, 8445.
[5] Peyroux, E.; Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2004, 1075.
[6] (a) Mayer, M.; Czaplik, W. M.; Jacobi von Wangelin, A. Adv. Synth. Catal. 2010, 352, 2147.
(b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359.
[7] (a) Miller, J.; Dankwardt, J.; Penney, J. Synthesis 2003, 2003, 1643.
(b) Rollin, Y.; Meyer, G.; Troupel, M.; Fauvarque, J.-F.; Perichon, J. J. Chem. Soc., Chem. Commun. 1983, 793.
[8] (a) Brown, H. C.; Basavaiah, D.; Kulkarni, S. U.; Bhat, N. G.; Prasad, J. V. N. V. J. Org. Chem. 1988, 53, 239.
(b) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
(c) Kondo, H.; Kageyama, A.; Yamaguchi, Y.; Haga, M.-A.; Kirchner, K.; Nagashima, H. Bull. Chem. Soc. Jpn. 2001, 74, 1927.
(d) Nagaki, A.; Moriwaki, Y.; Haraki, S.; Kenmoku, A.; Takabayashi, N.; Hayashi, A.; Yoshida, J. Chem. Asian J. 2012, 7, 1061.
[9] Colberg, J. C.; Rane, A.; Vaquer, J.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 115, 6065.
[10] Hassam, M.; Tahir, A.; Arnot, G. E.; Green, I. R.; Van Otterlo, W. A. L. Chem. Rev. 2015, 115, 5462.
[11] (a) Luu, T. X.; Lam, T. T.; Le, T. N.; Duus, F. Molecules 2009, 14, 3411.
(b) Waldman, S. R.; Monte, A. P.; Bracey, A.; Nichols, D. E. Tetrahedron Lett. 1996, 37, 7889.
[12] Lee, H. S.; Lee, G. Y. Bull. Korean Chem. Soc. 2005, 26, 461.
[13] (a) Reddy, M. R.; Periasamy, M. J. Organomet. Chem. 1995, 491, 263.
(b) Casey, C. P.; Cyr, C. R. J. Am. Chem. Soc. 1973, 95, 2248.
[14] Setty-Fichman, M.; Sasson, Y.; Blum, J. J. Mol. Catal. A: Chem. 1997, 126, 27.
[15] (a) Donohoe, T. J.; O'Riordan, T. J.; Rosa, C. P. Angew. Chem., Int. Ed. 2009, 48, 1014.
(b) Sharma, S. K.; Srivastava, V. K.; Jasra, R. V. J. Mol. Catal. A: Chem. 2006, 245, 200.
[16] (a) Biswas, S.; Huang, Z.; Choliy, Y.; Wang, D. Y.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2012, 134, 13276.
(b) Chianese, A. R.; Shaner, S. E.; Tendler, J. A.; Pudalov, D. M.; Shopov, D. Y.; Kim, D.; Rogers, S. L.; Mo, A. Organometallics 2012, 31, 7359.
(c) Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Chem. Soc., Chem. Commun. 1976, 716.
(d) Ge'rard, H. l.; Eisenstein, O.; Lee, D.-H.; Chen, J.; Crabtree, R. H. New J. Chem. 2001, 25, 1121.
[17] Scarso, A.; Colladon, M.; Sgarbossa, P.; Santo, C.; Michelin, R. A.; Strukul, G. Organometallics 2010, 29, 1487.
[18] (a) Bricout, H.; Mortreux, A.; Monflier, E. J. Organomet. Chem. 1998, 553, 469.
(b) Jinesh, C. M.; Antonyraj, C. A.; Kannan, S. Catal. Today 2009, 141, 176.
(c) Tolman, C. A. J. Am. Chem. Soc. 1972, 94, 2994.
[19] (a) Sui-Seng, C.; Groux, L. F.; Zargarian, D. Organometallics 2006, 25, 571.
(b) Lim, H. J.; Smith, C. R.; RajanBabu, T. V. J. Org. Chem. 2009, 74, 4565.
(c) Kim, I. S.; Dong, G. R.; Jung, Y. H. J. Org. Chem. 2007, 72, 5424.
(d) Jennerjahn, R.; Piras, I.; Jackstell, R.; Franke, R.; Wiese, K. D.; Beller, M. Chem. Eur. J. 2009, 15, 6383.
(e) Fan, J.; Wan, C.; Wang, Q.; Gao, L.; Zheng, X.; Wang, Z. Org. Biomol. Chem. 2009, 7, 3168.
[20] (a) Myagmarsuren, G.; Tkach, V. S.; Shmidt, F. K.; Mohamad, M.; Suslov, D. S. J. Mol. Catal. A: Chem. 2005, 235, 154.
(b) Gandeepan, P.; Cheng, C. H. J. Am. Chem. Soc. 2012, 134, 5738.
(c) Ma, H.; Sun, Q.; Li, W.; Wang, J.; Zhang, Z.; Yang, Y.; Lei, Z. Tetrahedron Lett. 2011, 52, 1569.
[21] (a) Jia, C. Science 2000, 287, 1992.
(b) Wang, Y. F.; Gao, Y. R.; Mao, S.; Zhang, Y. L.; Guo, D. D.; Yan, Z. L.; Guo, S. H.; Wang, Y. Q. Org. Lett. 2014, 16, 1610.
(c) Bedford, R. B.; Haddow, M. F.; Mitchell, C. J.; Webster, R. L. Angew. Chem., Int. Ed. 2011, 50, 5524.
[22] (a) Gauthier, D.; Lindhardt, A. T.; Olsen, E. P.; Overgaard, J.; Skrydstrup, T. J. Am. Chem. Soc. 2010, 132, 7998.
(b) Wu, Q.; Wang, L.; Jin, R.; Kang, C.; Bian, Z.; Du, Z.; Ma, X.; Guo, H.; Goa, L. Eur. J. Org. Chem. 2016, 5415.
(c) Shu, L.; Shi, Y. Tetrahedron Letters, 2004, 45, 8115.
(d) Hakim siddiqi, S. M. A.; Touchy, A. S.; Kon, K.; Shimizu, K.-C. Chem. Eur. J. 2016, 22, 6111.
(e) Simonetti, S. O.; Largh, E. L.; Kaufman, T. S. Org. Biomol. Chem. 2014, 12, 3735.
(f) Xie, W.; Chang, X. Angew. Chem., Int. Ed. 2016, 55, 1876.
(g) Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2013, 52, 1739.
(h) Fornes, V.; Garcia, H.; Marti, V.; Fernadez, L. Tetrahedron 1998, 54, 3827.
(i) Baker, W.; Flemons, G. F. J. Chem. Soc. 1948, 1984.
[23] (a) Albéniz, A. C.; Epsinet, P.; Lin, Y.-S. Organometallics 1995, 14, 2977.
(b) Trost, M. B.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427.

钯/对甲苯磺酸催化烯丙基苯异构化合成β-甲基苯乙烯衍生物的方法研究（英文）

Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes

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