Lewis base-assisted Lewis acid-catalyzed selective alkene formation via alcohol dehydration and synthesis of 2-cinnamyl-1,3-dicarbonyl compounds from 2-aryl-3,4-dihydropyrans

doi:10.1016/S1872-2067(15)61084-1

Abstract

Abstract:

Acid-catalyzed dehydration of alcohols has been widely employed for the synthesis of alkenes. However, activated alcohols when employed as substrates in dehydration reactions are often plagued by the lack of alkene selectivity. In this work, the reaction system can be significantly improved through enhancing the performance of Lewis acid catalysts in the dehydration of activated alcohols by combining with a Lewis base. Observations of the reaction mechanism revealed that the Lewis base component might have changed the reaction rate order. Although both the principal and side reaction rates decreased, the effect was markedly more observed on the latter reaction. Therefore, the selectivity of the dehydration reaction was improved. On the basis of this observation, a new route to synthesize 2-cinnamyl-1,3-dicarbonyl compounds was developed by using 2-aryl-3,4- dihydropyran as a starting substrate in the presence of a Lewis acid/Lewis base combined catalyst system.

Key words: Synergistic catalysis, Acid-base catalysis, Dehydration of alcohol, 2-Cinnamyl-1,3-dicarbonyl compound, Homogeneous catalysis

Changhui Liu, Bin Pan, Yanlong Gu. Lewis base-assisted Lewis acid-catalyzed selective alkene formation via alcohol dehydration and synthesis of 2-cinnamyl-1,3-dicarbonyl compounds from 2-aryl-3,4-dihydropyrans[J]. Chinese Journal of Catalysis, 2016, 37(6): 979-986.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(15)61084-1

https://www.cjcatal.com/EN/Y2016/V37/I6/979

References

[1] A. Molnar, M. Bartok, in: R. A. Sheldon, H. Van Bekkum eds, Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2001, 295.
[2] J. K. F. Buijink, J. P. Lange, A. N. R. Bos, A. D. Horton, F. G. M. Niele, in: S. T. Oyama ed, Mechanisms in Homogeneous and Heterogeneous Epoxidation Catalysis, Elsevier B. V., Amsterdam, 2008, 355.
[3] J. P. Lange, V. Otten, Ind. Eng. Chem. Res., 2007, 46, 6899-6903.
[4] J. P. Perez Valencia, E. San Nicolas Sayans, Ind. Eng. Chem. Res., 2011, 50, 5485-5489.
[5] N. M. Bertero, A. F. Trasarti, C. R. Apesteguia, A. J. Marchi, Appl. Catal. A, 2013, 458, 28-38.
[6] Z. Hasan, J. S. Hwang, S. H. Jhung, Catal. Commun., 2012, 26, 30-33.
[7] N. M. Bertero, C. R. Apesteguia, A. J. Marchi, Catal. Commun., 2008, 10, 261-265.
[8] T. J. Korstanje, J. T. B. H. Jastrzebski, R. J. M. Klein Gebbink, ChemSusChem, 2010, 3, 695-697.
[9] M. L. Kantam, P. L. Santhi, M. F. Siddiqui, Tetrahedron Lett., 1993, 34, 1185-1186.
[10] T. Nishiguchi, N. Machida, E. Yamamoto, Tetrahedron Lett., 1987, 28, 4565-4568.
[11] H. A. Kalviri, F. M. Kerton, Adv. Synth. Catal., 2011, 353, 3178-3186.
[12] Z. Zhu, J. H. Espenson, J. Org. Chem., 1996, 61, 324-328.
[13] C. H. Liu, M. Shen, B. B. Lai, A. Taheri, Y. L. Gu, ACS Comb. Sci., 2014, 16, 652-660.
[14] M. M. Heravi, T. Ahmadi, A. Fazeli, N. M. Kalkhorani, Curr. Org. Synth., 2015, 12, 328-357.
[15] A. Tarlani, A. Riahi, M. Abedini, M. M. Amini, J. Muzart, J. Mol. Catal. A, 2006, 260, 187-189.
[16] A. A. H. F. Lafi, S. K. Matam, H. A. Hodali, Ind. Eng. Chem. Res., 2015, 54, 3754-3760.
[17] D. Mochizuki, R. Sasaki, M. M. Maitani, M. Okamoto, E. Suzuki, Y. Wada, J. Catal., 2015, 323, 1-9.
[18] P. Vazquez, L. Pizzio, C. Caceres, M. Blanco, H. Thomas, E. Alesso, L. Finkielsztein, B. Lantãno, G. Moltrasio, J. Aguirre, J. Mol. Catal. A, 2000, 161, 223-232.
[19] E. C. Wijnbelt, E. H. Hekelaar, US Patent, 20100240939 A1, 2010.
[20] N. M. Bertero, A. F. Trasarti, C. R. Apesteguia, A. J. Marchi, Appl. Catal. A, 2013, 458, 28-38.
[21] Y. M. Wang, V. Ulrich, G. F. Donnelly, F. Lorenzini, A. C. Marr, P. C. Marr, ACS Sustain. Chem. Eng., 2015, 3, 792-796.
[22] J. A. Ma, D. Cahard, Angew. Chem. Int. Ed., 2004, 43, 4566-4583.
[23] A. G. Doyle, E. N. Jacobsen, Chem. Rev., 2007, 107, 5713-5743.
[24] S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev., 2007, 107, 5471-5569.
[25] M. Shibasaki, N. Yoshikawa, Chem. Rev., 2002, 102, 2187-2209.
[26] D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res., 2008, 41, 655-663.
[27] M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett, 2005, 1491-1508.
[28] S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed., 2008, 47, 1560-1638.
[29] H. Yamamoto, K. Futatsugi, Angew. Chem. Int. Ed., 2005, 44, 1924-1942.
[30] H. Yamamoto, K. Futatsugi, in: H. Yamamoto, K. Ishihara eds, Acid Catalysis in Modern Organic Synthesis, Wiley-VCH, Weinheim, 2008, 1.
[31] L. J. Min, B. Pan, Y. L. Gu, Org. Lett., 2016, 18, 364-367.
[32] C. H. Liu, L. Zhou, W. B. Huang, M. Wang, Y. L. Gu, Adv. Synth. Catal., 2016, 358, 900-918.
[33] S. Kamijo, Y. Yamamoto, in: M. Shibasaki, Y. Yamamoto eds, Multimetallic Catalysts in Organic Synthesis, Wiley-VCH, Weinheim, 2004, 1.
[34] H. Li, H. G. Wu, Q. Y. Zhang, J. Liu, X. F. Liu, Y. C. Liu, S. Yang, Curr. Catal., 2013, 2, 173-212.
[35] C. H. Liu, L. Zhou, D. Jiang, Y. L. Gu, Asian J. Org. Chem., 2016, 5, 367-372.
[36] H. Morimoto, T. Yoshino, T. Yukawa, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed., 2008, 47, 9125-9129.
[37] S. E. Denmark, Y. Ueki, Organometallics, 2013, 32, 6631-6634.
[38] R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc., 2010, 132, 5522-5531.
[39] D. Uraguchi, N. Kinoshita, D. Nakashima, T. Ooi, Chem. Sci., 2012, 3, 3161-3164.
[40] C. H. Liu, A. Taheri, B. B. Lai, Y. L. Gu, Catal. Sci. Technol., 2015, 5, 234-245.
[41] M. H. Li, Y. L. Gu, Adv. Synth. Catal., 2012, 354, 2484-2494.
[42] Z. Q. Liu, Y. X. Zhang, L. X. Zhao, Z. J. Li, J. T. Wang, H. J. Li, L. M. Wu, Org. Lett., 2011, 13, 2208-2211.
[43] A. Taheri, C. H. Liu, B. B. Lai, C. Cheng, X. J. Pan, Y. L. Gu, Green Chem., 2014, 16, 3715-3719.
[44] K. X. Zeng, Z. P. Huang, J. Yang, Y. L. Gu, Chin. J. Catal., 2015, 36, 1606-1613.
[45] A. Taheri, B. B. Lai, C. Cheng, Y. L. Gu, Green Chem., 2015, 17, 812-816.
[46] J. R. Cabrero-Antonino, A. Leyva-Perez, A. Corma, Chem. Eur. J., 2013, 19, 8627-8633.
[47] N. G .Grigor'eva, S. V. Bubennov, L. M. Khalilov, B. I. Kutepov, Appl. Catal. A, 2011, 407, 85-90.
[48] T. J. Korstanje, J. T. B. H. Jastrzebski, R. J. M. Klein Gebbink, Chem. Eur. J., 2013, 19, 13224-13234.
[49] T. Aoyama, S. Koda, Y. Takeyoshi, T. Ito, T. Takido, M. Kodomari, Chem. Commun., 2013, 49, 6605-6607.
[50] F. Han, L. Yang, Z. Li, Y. W. Zhao, C. G. Xia, Adv. Synth. Catal., 2014, 356, 2506-2516.
[51] A. Taheri, X. J. Pan, C. H. Liu, Y. L. Gu, ChemSusChem, 2014, 7, 2094-2098.
[52] W. Yang, L. L. Huang, H. Liu, W. Wang, H. Li, Chem. Commun., 2013, 49, 4667-4669.
[53] R. Nallagonda, R. R. Reddy, P. Ghorai, Chem. Eur. J., 2015, 21, 14732-14736.
[54] C. P. Wang, F. Ye, C. G. Wu, Y. Zhang, J. B. Wang, J. Org. Chem., 2015, 80, 8748-8757.
[55] R. Panish, S. R. Chintala, D. T. Boruta, Y. Z. Fang, M. T. Taylor, J. M. Fox, J. Am. Chem. Soc., 2013, 135, 9283-9286.
[56] T. Cuvigny, M. Julia, J. Organometal. Chem., 1987, 331, 121-137.
[57] C. M. Qin, H. M. L. Davies, Org. Lett., 2013, 15, 310-313.
[58] M. Yasuda, T. Somyo, A. Baba, Angew. Chem. Int. Ed., 2006, 45, 793-796.
[59] M. Rueping, B. J. Nachtsheim, A. Kuenkel, Org. Lett., 2007, 9, 825-828.
[60] J. Tsuji, I. Shimizu, I. Minami, Y. Ohashi, T. Sugiura, K. Takahashi, J. Org. Chem., 1985, 50, 1523-1529.
[61] G. Giambastiani, G. Poli, J. Org. Chem., 1998, 63, 9608-9609.
[62] T. Mitsudome, K. Nose, K. Mori, T. Mizugaki, K. Ebitani, K. Kitsukawa, K. Kaneda, Angew. Chem. Int. Ed., 2007, 46, 3288-3290.
[63] R. Shibuya, L. Lin, Y. Nakahara, K. Mashima, T. Ohshima, Angew. Chem. Int. Ed., 2014, 53, 4377-4381.
[64] S. Lin, C. X. Song, G. X. Cai, W. H. Wang, Z. J. Shi, J. Am. Chem. Soc., 2008, 130, 12901-12903.
[65] Y. L. Gu, J. Barrault, F. Jerome, Adv. Synth. Catal., 2009, 351, 3269-3278.
[66] Y. L. Gu, R. De Sousa, G. Frapper, C. Bachmann, J. Barrault, F. Jerome, Green Chem., 2009, 11, 1968-1972.
[67] M. H. Li, A. Taheri, M. Liu, S. H. Sun, Y. L. Gu, Adv. Synth. Catal., 2014, 356, 537-556.
[68] M. H. Li, C. H. Tang, J. Yang, Y. L. Gu, Chem. Commun., 2011, 47, 4529-4531.
[69] M. H. Li, Y. L. Gu, Tetrahedron, 2011, 67, 8314-8320.
[70] Y. J. Ren, M. H. Li, J. Yang, J. J. Peng, Y. L. Gu, Adv. Synth. Catal., 2011, 353, 3473-3484.