苯并富烯合成方法研究进展

doi:10.6023/cjoc201910029

有机化学 ›› 2020, Vol. 40 ›› Issue (4): 817-830.DOI: 10.6023/cjoc201910029 上一篇下一篇

所属专题：有机光催化虚拟合辑

综述与进展

苯并富烯合成方法研究进展

史传星^a,b, 冯陈国^b,c, 陈雅丽^a, 张曙盛^b,c, 林国强^b

a 上海大学理学院上海 200444;
b 中国科学院上海有机化学研究所天然产物有机合成化学重点实验室上海 200032;
c 上海中医药大学创新中药研究院上海 201203

收稿日期:2019-10-25 修回日期:2019-12-17 发布日期:2020-01-03
通讯作者: 陈雅丽, 张曙盛 E-mail:ylchen@staff.shu.edu.cn;zhangss@sioc.ac.cn
基金资助:
国家自然科学基金（Nos.221572253，21772216）、中国科学院战略性先导科技专项（No.XDB20020100）、中国科学院前沿科学重点研究（No.QYZDYSSWSLH026）资助项目.

Recent Advancement in Benzofulvene Synthesis

Shi Chuanxing^a,b, Feng Chenguo^b,c, Chen Yali^a, Zhang Shusheng^b,c, Lin Guoqiang^b

a College of Sciences, Shanghai University, Shanghai 200444;
b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Innovation Research Instutute of Tranditional Chinese Medicine, Shanghai University of Tranditional Chinese Medicine, Shanghai 201203

Received:2019-10-25 Revised:2019-12-17 Published:2020-01-03
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572253, 21772216), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB 20020100), and the Key Research Program of Frontier Science (No. QYZDY-SSWSLH026).

文章分享

摘要/Abstract

苯并富烯结构存在于许多天然分子和生物活性分子中，同时此类分子常常作为重要的合成砌块运用于材料科学和金属有机化学等领域.对苯并富烯的合成已进行了大量研究，尤其是近二十年的快速发展，已经发展了系列高效的合成方法.依据关键骨架构建反应引发机制的不同，这些方法大致可分为五大类：热引发或者光催化的双自由基机理的环化反应、过渡金属催化的串联环化反应、亲核或亲电试剂进攻引发的环化反应、自由基引发的环化反应以及酸促进的环化反应.本文将根据上述不同反应类型综述近些年苯富烯合成的研究进展.

关键词: 苯并富烯, 过渡金属催化, 双自由基, C—H键活化, 环化反应

Benzofulvenes were widely found in natural products and bioactive molecules, and also served as important building blocks in material science and transition-metal chemistry. Great efforts have been devoted to the efficient synthesis of these interesting molecules, and rapid advancement has been made in the past two decades. According to the types of the initiation of the reaction, these methods can roughly be classified into five categories:thermal or photochemical cyclization of enyne-al-lenes or enediynes, transition metal-catalyzed sequential cyclization reaction, electrophilic or nucleophilic attack initiated cyclization, radical initiated cyclization and acid promoted cyclization. This review describes the important synthetic methods of benzofulvenes according to their reaction types.

Key words: benzofulvenes, transition metal catalysis, radical, C—H bond activation, cyclization reaction

引用此文

史传星, 冯陈国, 陈雅丽, 张曙盛, 林国强. 苯并富烯合成方法研究进展[J]. 有机化学, 2020, 40(4): 817-830.

Shi Chuanxing, Feng Chenguo, Chen Yali, Zhang Shusheng, Lin Guoqiang. Recent Advancement in Benzofulvene Synthesis[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 817-830.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Thiele, J. Chem. Ber. 1900, 33, 666.
[2] Yates, P. V. Adv. Alicyclic Chem. 1968, 2, 59.
[3] Simple examples for application, see:(a) Kosaka, Y.; Kitazawa, K.; Inomata, S.; Ishizone, T. ACS Macro Lett. 2013, 2, 164.
(b) Cappelli, A.; Galeazzi, S.; Giuliani, G.; Anzini, M.; Grassi, M.; Lapasin, R.; Grassi, G.; Farra, R.; Dapas, B.; Aggravi, M.; Donati, A.; Zetta, L.; Boccia, A. C.; Bertini, F.; Samperi, F.; Vomero, S. Macromolecules 2009, 42, 2368.
[4] (a) Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993.
(b) Shanmugam P.; Rajasingh, P. Chem. Lett. 2005, 34, 1494.
[5] (a) Walters, M. J.; Blobaum, A. L.; Kingsley, P. J.; Felts, A. S.; Sulikowski, G. A.; Marnett, L. J. Bioorg. Med. Chem. Lett. 2009, 19, 3271.
(b) Felts, A. S.; Siegel, B. S.; Young, S. M.; Moth, C. W.; Lybrand, T. P.; Dannenberg, A. J.; Marnett, L. J.; Subbaramaiah, K. J. Med. Chem. 2008, 51, 4911.
(c) Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 2397.
(d) Maguire, A. R.; Papot, S.; Ford, A.; Touhey, S.; O'Connor, R.; Clynes, M. Synlett 2001, 41.
[6] (a) Snyder, S. A.; Zografos, A. L.; Lin, Y. Angew. Chem., Int. Ed. 2007, 46, 8186.
(b) Jeffrey, J. L.; Sarpong, R. Tetrahedron Lett. 2009, 50, 1969.
(c) Singer, R. A.; McKinley, J. D.; Barbe, G.; Farlow, R. A. Org. Lett. 2004, 6, 2357.
[7] (a) Cappelli, A.; Galeazzi, S.; Giuliani, G.; Anzini, M.; Donati, A.; Zetta, L.; Mendichi, R.; Aggravi, M.; Giorgi, G.; Paccagnini, E.; Vomero, S. Macromolecules 2007, 40, 3005.
(b) Cappelli, A.; Galeazzi, S.; Giuliani, G.; Anzini, M.; Grassi, M.; Lapasin, R.; Grassi, G.; Farra, R.; Dapas, B.; Aggravi, M.; Donati, A.; Zetta, L.; Boccia, A. C.; Bertini, F.; Samperi, F.; Vomero, S. Macromolecules 2009, 42, 2368.
(c) Cappelli, A.; Paolino, M.; Grisci, G.; Giuliani, G.; Donati, A.; Mendichi, R.; Boccia, A. C.; Botta, C.; Mroz, W.; Samperi, F.; Scamporrino, A.; Giorgi, G.; Vomero, S. J. Mater. Chem. 2012, 22, 9611.
(d) Kosaka, Y.; Kitazawa, K.; Inomata, S.; Ishizone, T. ACS Macro Lett. 2013, 2, 164.
(e) Cappelli, A.; Villafiorita-Monteleone, F.; Grisci, G.; Paolino, M.; Razzano, V.; Fabio, G.; Giuliani, G.; Donati, A.; Mendichi, R.; Boccia, A. C.; Pasini, M.; Botta, C. J. Mater. Chem. C 2014, 2, 7897.
(f) Cappelli, A.; Razzano, V.; Paolino, M.; Grisci, G.; Giuliani, G.; Donati, A.; Mendichi, R.; Samperi, F.; Battiato, S.; Boccia, A. C.; Mura, A.; Bongiovanni, G.; Mroz, W.; Botta, C. Polym. Chem. 2015, 6, 7377.
(g) Kosaka, Y.; Kawauchi, S.; Goseki, R.; Ishizone, T. Macro-molecules 2015, 48, 4421.
(h) Wang, W.; Schlegel, R.; White, B. T.; Williams, K.; Voyloy, D.; Steren, C. A.; Goodwin, A.; Coughlin, E. B.; Gido, S.; Beiner, M.; Hong, K.; Kang, N.-G.; Mays, J. Macromolecules 2016, 49, 2646.
(i) Chen. S.-D.; Li, Q.-P.; Sun, S.-Y.; Ding, Y.; Hu, A.-H. Macromolecules 2017, 50, 534.
[8] (a) Fischer, M.; Oswald, T.; Ebert, H.; Schmidtmann, M.; Beckhaus, R. Organometallics 2018, 37, 415.
(b) Rogers, J. S.; Lachicotte, R. J.; Bazan, G. C. Organometallics 1999, 18, 3976.
[9] Habaue, S.; Sakamoto, H.; Okamoto, Y. Polym. J. 1997, 29, 384.
[10] Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079.
[11] Yuki, K.; Susumu, K.; Raita, K.; Takashi, I. Macromolecules 2015, 48, 4421.
[12] Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
[13] (a) Mers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057.
(b) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995.
[14] Matthias, P.; Alexander, W.; Peter, R. S. J. Phys. Chem. A 2001, 105, 9265.
[15] Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975.
[16] Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691.
(b) Schmittel, M.; Maywald, M.; Strittmatter, M. Synlett 1997, 165.
[17] Igor, V. A.; Serguei, V. K. J. Am. Chem. Soc. 2002, 124, 9052
[18] Schmittel, M.; Mahajan, A. A.; Bucher, G.; Bats, J. W. J. Org. Chem. 2007, 72, 2166.
[19] Vavilala, C.; Byrne, N.; Kraml, C. M.; Douglas, M.; Pascal, J. R. J. Am. Chem. Soc. 2008, 130, 13549.
[20] Bucher, G.; Mahajan, A.; Schmittel, M. J. Org. Chem. 2008, 73, 8815.
[21] Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.; Endo, K.; Shibata, T. J. Organomet. Chem. 2008, 693, 3939.
[22] Tsuchikama, K.; Kasagawa, M.; Endo, K.; Shibata, T. Synlett 2010, 1, 97.
[23] Patureau, F, W.; Besset, T.; Kuhl, T.; Glorius, J. F. J. Am. Chem. Soc. 2011, 133, 2154.
[24] (a) Chinnagolla, R. K.; Jeganmohan, M. Eur. J. Org. Chem. 2012, 417.
(b) Yu, Y.; Wu, Q.; Liu, D.; Hu, L.; Yu, L.; Tan, Z.; Zhu, G. J. Org. Chem. 2019, 84, 7449.
[25] Guo, B.; Zheng, L.Y.; Zheng, Z. L.; Hua, R. M. J. Org. Chem. 2015, 80, 8430.
[26] Raju, S.; Hsiao, H.-C.; Thirupathi, S.; Chen, P.-L.; Chuang, S.-C. Adv. Synth. Catal. 2019, 361, 683.
[27] Dyker, G.; Nerenz, F.; Siemsen, P.; Bubenitschek, P.; Jones, P. G. Chem. Ber. 1996, 1265.
[28] Singer, R. A.; McKinley, J. D.; Barbe, G.; Farlow, R. A. Org. Lett. 2004, 6, 2357.
[29] Furuta, T.; Asakawa, T.; Iinuma, M.; Fujii, S.; Tanaka, K.; Kan, T. Chem. Commun. 2006, 3648.
[30] Abdur Rahman, S. M.; Sonoda, M.; Ono, M.; Miki, K.; Tobe, Y., Org. Lett. 2006, 8, 1197.
[31] Li, C.-K.; Zeng, Y.; Wang, J.-B. Tetrahedron Lett. 2009, 50, 2956.
[32] Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 5406.
[33] (a) Ye, S.-Q.; Yang X.-D.; Wu, J. Chem. Commun. 2010, 46, 2950.
(b) Ye, S.-Q.; Ren, H.; Wu, J. J. Comb. Chem. 2010, 12, 670.
[34] Bryan C. S.; Lautens, M. Org. Lett. 2010, 12, 2754.
[35] Kim, K. H.; Kim, S. H.; Park, B. R.; Kim, J.-N. Tetrahedron Lett. 2010, 51, 3368.
[36] Lim, C. H.; Kim, K. H.; Lim, J. W.; Kim, J. N. Tetrahedron Lett. 2013, 54, 5808.
[37] (a) Wang, W.-Y.; Sun, L. L.; Deng, C. L.; Tang, R.-Y.; Zhang, X.-G. Synthesis 2013, 45, 118.
(b) Zhang, T.; Chen, F.; Zhang, X.-H.; Qian, P.-C.; Zhang, X.-G. J. Org. Chem. 2019, 84, 307.
[38] (a) Álvarez, E.; Miguel, D.; García-García, P.; Fernández-Rodríguez, M. A.; Rodríguez, F.; Sanz, R. Synthesis 2012, 44, 1874.
(b) Alvarez, E.; Nieto Faza, O.; Silva Lopez, C.; Fernandez-Rodri-guez, M. A.; Sanz, R. Chem.-Eur. J. 2015, 21, 12889.
[39] Chen, Z.; Jia, X.; Huang, J.; Yuan, J. J. Org. Chem. 2014, 79, 10674.
[40] Hou, Q. W.; Zhang, Z. H.; Kong, F. J.; Wang, S. Z.; Wang, H. Q.; Yao, Z. J. Chem. Commun. 2013, 49, 695.
[41] Aziz, J.; Brion, J.-D.; Alami, M.; Hamze, A. RSC Adv. 2015, 5, 74391.
[42] Shin, S.; Son, J. Y.; Choi, C.; Kim, S.; Lee, P. H. J. Org. Chem. 2016, 81, 11706.
[43] Zhou, B.; Wu, Z.; Qi, W.; Sun, X.; Zhang, Y. Adv. Synth. Catal. 2018, 360, 4480.
[44] Peng, J.-B.; Wu, F.-P.; Spannenberg, A.; Wu, X.-F. Chem. Eur. J. 2019, 25, 8696.
[45] Borthakur, S.; Baruah, S.; Sarma, B.; Gogoi, S. Org. Lett. 2019, 21, 2768.
[46] (a) Hashmi, A. S. K.; Braun, I.; Noesel, P.; Schaedlich, J.; Wieteck, M.; Rudolph, M.; Rominger, F. Angew. Chem., Int. Ed. 2012, 51, 4456.
(b) Plajer, A; Ahrens, L.; Wieteck, M.; Lustosa, D. M.; Babaahmadi, R.; Yates, B.; Ariafard, A.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Chem.-Eur. J. 2018, 24, 10766.
[47] Salacz, L.; Girard, N.; Suffert, J.; Blond, G. Molecules 2019, 24, 595.
[48] Whitlock, H. W.; Sandvick, P. E.; Overman, L. E.; Reichardt, P. B. J Org. Chem. 1969, 34, 879.
[49] (a) Schreiner, P. R.; Prall, M.; Lutz, V. Angew. Chem., Int. Ed. 2003, 42, 5757.
(b) Garcia-Garcia, P.; Sanjuan, A. M.; Rashid, M. A.; Martinez-Cuezva, A.; Fernandez-Rodriguez, M. A.; Rodriguez, F.; Sanz, R. J. Org. Chem. 2017, 82, 1155.
[50] Huang, X.; Yang, Y. Org. Lett. 2007, 9, 1667.
[51] Xiao, Q.; Zhu, H.; Li, G.; Chen, Z. Adv. Synth. Catal. 2014, 356, 3809.
[52] Martinelli, C.; Cardone, A.; Pinto, V.; Mastropasqua Talamo, M.; D'Arienzo, M. L.; Mesto, E.; Schingaro, E.; Scordari, F.; Naso, F.; Musio, R.; Farinola, G. M. Org. Lett. 2014, 16, 3424.
[53] König, B.; Pitsch, W.; Klein, M.; Vasold, R.; Prall, M.; Schreiner, P. R. J. Org. Chem. 2001, 66, 1742.
[54] Kovalenko, S. V.; Peabody, S.; Manoharan, M.; Clark, R. J.; Alabugin, I. V. Org. Lett. 2004, 6, 2457.
[55] Peabody, S. W.; Breiner, B.; Kovalenko, S. V.; Patil, S.; Alabugin, I. V. Org. Biomol. Chem. 2005, 3, 218.
[56] Qin, X.-Y.; He, L.; Li, J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2019, 55, 3227.
[57] Cordier, P.; Aubert, C.; Malacria, M.; Lacote, E.; Gandon, V. Angew. Chem., Int. Ed. 2009, 48, 8757.
[58] Sousa, C. M.; Berthet, J.; Delbaere, S.; Coelho P. J. J. Org. Chem. 2014, 79, 5781.
[59] Sai, M.; Matsubara, S. Synlett 2014, 25, 2067.
[60] Warner, A. J.; Enright, K. M.; Cole, J. M.; Yuan, K.; McGough, J. S.; Ingleson, M. J. Org. Biomol. Chem. 2019, 17, 5520.

苯并富烯合成方法研究进展

Recent Advancement in Benzofulvene Synthesis

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.
[2]	高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.
[3]	张素珍, 张文文, 杨慧, 顾庆, 游书力. 铑催化2-烯基苯酚与炔烃的对映体选择性螺环化反应[J]. 有机化学, 2023, 43(8): 2926-2933.
[4]	陈新强, 张敬. 伯醇的脱羟甲基反应的研究进展[J]. 有机化学, 2023, 43(8): 2711-2719.
[5]	陈玉琢, 孙红梅, 王亮, 胡方芝, 李帅帅. 基于α-氢迁移策略构建杂环骨架的研究进展[J]. 有机化学, 2023, 43(7): 2323-2337.
[6]	徐光利, 许静, 徐海东, 崔香, 舒兴中. 过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展[J]. 有机化学, 2023, 43(6): 1899-1933.
[7]	孙李星, 孙婷婷, 王海清, 吴淑芳, 王小烨, 刘天雅, 张宇辰. Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应[J]. 有机化学, 2023, 43(6): 2178-2188.
[8]	任志军, 罗维纬, 周俊. 银介导的N-芳基丙烯酰胺串联环化反应研究进展[J]. 有机化学, 2023, 43(6): 2026-2039.
[9]	户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真. 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023, 43(6): 2239-2244.
[10]	庞明杨, 常宏宏, 冯璋, 张娟. 过渡金属催化吲哚的串联去芳构化反应研究进展[J]. 有机化学, 2023, 43(4): 1271-1291.
[11]	李靖鹏, 黄顺桃, 杨棋, 李伟强, 刘腾, 黄超. 利用连续流动技术合成(Z)-N-乙烯基取代N,O-缩醛[J]. 有机化学, 2023, 43(4): 1550-1558.
[12]	南江, 黄冠杰, 胡岩, 王波. 钌催化喹唑啉酮与碳酸亚乙烯酯的C—H [4＋2]环化反应[J]. 有机化学, 2023, 43(4): 1537-1549.
[13]	蒙玲, 汪君. 硫代黄烷酮类衍生物的合成研究进展[J]. 有机化学, 2023, 43(3): 873-891.
[14]	段康慧, 唐俊龙, 伍婉卿. 稠杂环化合物的合成及其抗肿瘤活性研究进展[J]. 有机化学, 2023, 43(3): 826-854.
[15]	贾海瑞, 邱早早. 过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展[J]. 有机化学, 2023, 43(3): 1045-1068.