苯酚与烯烃的氧化环加成反应研究进展
收稿日期: 2016-07-10
修回日期: 2016-08-30
网络出版日期: 2016-09-08
基金资助
陕西省自然科学基金（No. 2011JQ2001）资助项目.
Recent Advances in Oxidative Cycloaddition Reactions of Phenols with Olefins
Received date: 2016-07-10
Revised date: 2016-08-30
Online published: 2016-09-08
Supported by
Project supported by the National Natural Science Foundation of Shaanxi Province(No. 2011JQ2001).
崔娜 , 赵宇 , 王云侠 . 苯酚与烯烃的氧化环加成反应研究进展[J]. 有机化学, 2017 , 37(1) : 20 -30 . DOI: 10.6023/cjoc201607017
Phenol oxidation and the induced transformations can construct various core skeletons of bioactive molecules.Due to the extensive existence of dihydrobenzofuran core,which could be generated from the oxidative cycloaddtion reaction of phenols and olefins in bioactive neolignans and resveratrol oligomers,the oxidative cycloaddition reaction of phenols and olefins catched broad attention from organic chemists.Herein,the progress of oxidative cycloadditon reactions of phenols and olefins in recent years is reviewed according to the difference of reaction conditions,and the corresponding reaction mechanisms are discussed.
Key words： phenol; olefin; oxidative cycloaddition reaction; dihydrobenzofuran
[1] (a) Fan, R.; Ding, Q.; Ye, Y. Synthesis 2012, 45, 1.
(b) Su, B.; Deng, M.; Wang, Q. Org. Lett. 2013, 15, 1606.
[2] (a) Libman, A.; Shalit, H.; Vainer, Y.; Narute, S.; Kozuch, S.; Pappo, D. J. Am. Chem. Soc. 2015, 137, 11453.
(b) More, N. Y.; Jeganmohan, M. Org. Lett. 2015, 17, 3042.
(c) Matsushita, M.; Kamata, K.; Yamaguchi, K.; Mizuno, N. J. Am. Chem. Soc. 2005, 127, 6632.
(d) Morimoto, K.; Sakamoto, K.; Ohnishi, Y.; Miyamoto, T.; Ito, M.; Dohi, T.; Kita, Y. Chem. Eur. J. 2013, 19, 8726.
(e) Elsler, B.; Schollmeyer, D.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2014, 53, 5210.
(f) Lee, Y. E.; Cao, T.; Torruellas, C.; Kozlowski, M. C. J. Am. Chem. Soc. 2014, 136, 6782.
(g) Gaster, E.; Vainer, Y.; Regev, A.; Narute, S.; Sudheendran, K.; Werbeloff, A.; Shalit, H.; Pappo, D. Angew. Chem., Int. Ed. 2015, 54, 4198.
(h) Morimoto, K.; Sakamoto, K.; Ohshika, T.; Dohi, T.; Kita, Y. Angew. Chem., Int. Ed. 2016, 55, 3652.
[3] (a) Seoane, A.; Casanova, N.; Quinones, N.; Mascarenas, J. L.; Gulias, M. J. Am. Chem. Soc. 2014, 136, 7607.
(b) Zuo, Z.; Yang, X.; Liu, J.; Nan, J.; Bai, L.; Wang, Y.; Luan, X. J. Org. Chem. 2015, 80, 3349.
[4] (a) Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc. 2009, 131, 17387.
(b)Parnes, R.; Kshirsagar, U. A.; Werbeloff, A.; Regev, C.; Pappo, D. Org. Lett. 2012, 14, 3324.
(c)Pappo, D.; Regev, A.; Shalit, H. Synthesis 2015, 47, 1716.
[5] (a) Denizot, N.; Pouilhes, A.; Cucca, M.; Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G. Org. Lett. 2014, 16, 5752.
(b) Tomakinian, T.; Guillot, R.; Kouklovsky, C.; Vincent, G. Angew. Chem., Int. Ed. 2014, 53, 11881.
(c) Vincent, G.; Beaud, R.; Tomakinian, T.; Denizot, N.; Pouilhès, A.; Kouklovsky, C. Synlett 2014, 26, 432.
[6] Xu, W.; Nachtsheim, B. J. Org. Lett. 2015, 17, 1585.
[7] Lee, H.; Yi, C. S. Eur. J. Org. Chem. 2015, 9, 1899.
[8] (a) Jacquemot, G.; Ménard, M.-A.; L'Homme, C.; Canesi, S. Chem. Sci. 2013, 4, 1287.
(b) Long, R.; Yan, X.; Wu, Z.; Li, Z.; Xiang, H.; Zhou, X. Org. Biomol. Chem. 2015, 13, 3571.
[9] (a) Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Angew. Chem., Int. Ed. 2011, 50, 586.
(b) Chong, J.; Poutaraud, A.; Hugueney, P. Plant. Sci. 2009, 177, 143.
(c) Coy Barrera, E. D.; Cuca, S.; Aacute; rez, L. E. Chem. Pharm. Bull. 2009, 57, 639.
[10] Huang, Z.; Jin, L.; Feng, Y.; Peng, P.; Yi, H.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 7151.
[11] Tomakinian, T.; Guillot, R.; Kouklovsky, C.; Vincent, G. Angew. Chem., Int. Ed. 2014, 53, 11881.
[12] (a) Liang, K.; Yang, J.; Tong, X.; Shang, W.; Pan, Z.; Xia, C. Org. Lett. 2016, 18, 1474.
(b) Liang, K.; Wu, T.; Xia, C. Org. Biomol. Chem. 2016, 14, 4690.
[13] Kshirsagar, U. A.; Regev, C.; Parnes, R.; Pappo, D. Org. Lett. 2013, 15, 3174.
[14] Gaster, E.; Vainer, Y.; Regev, A.; Narute, S.; Sudheendran, K.; Werbeloff, A.; Shalit, H.; Pappo, D. Angew. Chem., Int. Ed. 2015, 54, 4198.
[15] Meng, L.; Zhang, G.; Liu, C.; Wu, K.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 10195.
[16] Blum, T. R.; Zhu, Y.; Nordeen, S. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 11056.
[17] Song, T.; Zhou, B.; Peng, G.W.; Zhang, Q.B.; Wu, L. Z.; Liu, Q.; Wang, Y. Chem.-Eur. J. 2014, 20, 678.
[18] Zhao, Y.; Huang, B.; Yang, C.; Li, B.; Xia, W. Synthesis 2015, 47, 2731.
[19] Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979.
[20] Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135.
[21] (a) Bérard, D.; Jean, A.; Canesi, S. Tetrahedron Lett. 2007, 48, 8238.
(b) Bérard, D.; Giroux, M. A.; Racicot, L.; Sabot, C.; Canesi, S. Tetrahedron 2008, 64, 7537.
(c) Bérard, D.; Racicot, L.; Sabot, C.; Canesi, S. Synlett 2008, 7, 1076.
(d) Sabot, C.; Bérard, D.; Canesi, S. Org. Lett. 2008, 10, 4629.
[22] Guérard, K. C.; Sabot, C.; Beaulieu, M. A.; Giroux, M. A.; Canesi, S. Tetrahedron 2010, 66, 5893.
[23] (a) Juhász, L.; Kürti, L.; Antus, S. J. Nat. Prod. 2000, 63, 866.
(b) Wang, E.; Weinb, Y.; Kuo Y. Tetrahedron Lett. 2006, 47, 9195.
[24] Mohr, A. L.; Lombardo, V. M.; Arisco, T. M.; Morrow, G. W. Synth. Commun. 2009, 39, 3845.
[25] Dohi, T.; Nakae, T.; Toyoda, Y.; Koseki, D.; Kubo, H.; Kamitanaka, T.; Kita, Y. Heterocycles 2015, 90, 631.
[26] Chen, P. Y.; Wu, Y. H.; Hsu, M. H.; Wang, T. P.; Wang, E. C. Tetrahedron 2013, 69, 653.
[27] Alvey, L.; Prado, S.; Huteau, V.; Saint-Joanis, B.; Michel, S.; Koch, M.; Cole, S.T.; Tillequin, F.; Janin Y. L. Bioorg. Med. Chem. 2008, 16, 8264.
[28] Shang, Y.; Qian, Y.; Liu, X.; Dai, F.; Shang, X.; Jia, W.; Liu, Q.; Fang, J.; Zhou, B. J. Org.Chem. 2009, 74, 5025.
[29] (a) Sako, M.; Hosokawa, H.; Ito, T.; Iinuma, M. J. Org. Chem. 2004, 69, 2598.
(b) Takaya, Y.; Terashima, K.; Ito, J.; He, Y. H.; Tateoka, M.; Yamaguchi, N.; Niwa, M. Tetrahedron 2005, 61, 10285.
(c) Bruschi, M.; Orlandi, M.; Rindone, B.; Rummakko, P.; Zoia, L. J. Phys. Org. Chem. 2006, 19, 592.
(d) Wang, G.; Wang, H.; Capretto, D. A.; Han, Q.; Hua, R.; Yang, S. Tetrahedron 2012, 68, 5216.
(e) Althagafy, H. S.; Meza-Aviña, M. E.; Oberlies, N. H.; Croatt, M. P. J. Org. Chem. 2013, 78, 7594.
(f) Magoulas, G. E.; Papaioannou, D. Molecules 2014, 19, 19769.
[30] Youn, S. W.; Eom, J. I. J. Org. Chem. 2006, 71, 6705.
[31] (a) El-Seedi, H. R.; Yamamura, S.; Nishiyama, S. Tetrahedron 2002, 58, 7485.
(b) Kirste, A.; Schnakenburg, G.; Stecker, F.; Fischer, A.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2010, 49, 971.
(c) El-Seedi, H. R.; Yamamura, S.; Nishiyama, S. Tetrahedron Lett. 2002, 43, 3301.
(d) Okada, Y.; Yshoka, T.; Koike, M.; Chiba, K. Tetrahedron Lett. 2011, 52, 4690.
(e) Chiba, K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem. 1999, 64, 7654.
(f) Kim, S.; Noda, S.; Hayashi, K.; Chiba, K. Org. Lett. 2008, 10, 1827.
[32] Bhusainahalli, V. M.; Spatafora, C.; Chalal, M.; Vervandier-Fasseur, D.; Meunier, P.; Latruffe, N.; Tringali, C. Eur. J. Org. Chem. 2012, 5217.
[33] (a) Nascimento, I. R.; Lopes, L. M. X.; Davin, L. B.; Lewis, N. G. Tetrahedron 2000, 56, 9181.
(b) Pereira, A. C.; Magalhaes, L. G.; Goncalves, U. O.; Luz, P. P.; Moraes, A. C. G.; Rodrigues, V.; Da Matta Guedes, P. M.; Da Silva Filho, A. A.; Cunha, W. R.; Bastos, J. K.; Nanayakkara, N. P. D.; E Silva, M. L. Phytochemistry 2011, 72, 1424.
(c) Syrjänen, K.; Brunow, G. Tetrahedron 2001, 57, 365.
(d) Toshiyuki,W.; Makoto, Nitta.; Kana, K.; Taketo, C.; Ye, Y.; Kuniro, T.; Toshiyuki, K.; Haruo, N.; Masaji, I.; Minako, K.; Yoshiaki, Y.; Yoshihide, S. Bioorg. Med. Chem. Lett. 2009, 19, 5905.
(e) Li, C.; Lu, J.; Xu, X.; Hu, R.; Pan, Y. Green Chem. 2012, 14, 328.
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