氧杂蒽类有机染料在可见光诱导有机合成中的应用

doi:10.6023/cjoc201805031

摘要/Abstract

氧杂蒽类有机染料作为光氧化还原催化剂，因具有廉价易得、水溶性好、反应活性高等优点被广泛应用于可见光诱导的有机合成中.其催化的有机反应类型不断被拓展，有逐渐取代部分过渡金属催化剂的趋势.根据反应类型进行分类，综述了近些年几种常用氧杂蒽类有机染料在光诱导有机合成中的研究进展，并对其前景进行了展望.

关键词: 有机染料, 光氧化还原, 有机合成, 过渡金属

Oxime organic dyes, acting as photoredox catalysts, are widely used in visible-light-induced organic synthesis due to their advantages of low cost, good water solubility, high reactivity and so on. The type of organic dyes-catalyzed organic reactions is continuously expanding, and there is a tendency that organic dyes are gradually replacing some of transition metal catalysts. Classified by the type of reactions, the research progress of several common organic dyes in visible-light-induced organic synthesis in recent years is reviewed, and their future outlook is also discussed.

Key words: organic dyes, photoredox, organic synthesis, transition metals

引用此文

徐雯秀, 戴小强, 徐涵靖, 翁建全. 氧杂蒽类有机染料在可见光诱导有机合成中的应用[J]. 有机化学, 2018, 38(11): 2807-2832.

Xu Wenxiu, Dai Xiaoqiang, Xu Hanjing, Weng Jianquan. Application of Oxime Organic Dyes in Visible-Light-Induced Organic Synthesis[J]. Chin. J. Org. Chem., 2018, 38(11): 2807-2832.

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

分享此文

参考文献

[1] (a) Ciamician, G. Sci. New Ser. 1912, 36, 385.
(b) Grätzel, M. Nature 2001, 414, 338.
(c) Nocera, A. Chem. Rev. 2007, 107, 4022.
(d) Albini, A.; Fagnoni, M. ChemSusChem 2008, 1, 63.
(e) Yum, J.-H.; Chen, P.; Gratzel, M.; Nazeeruddin, M. ChemSusChem 2008, 1, 699.
(f) Sala, X.; Romero, I.; Rodriguez, M.; Escriche, L.; Llobet, A. Angew. Chem., Int. Ed. 2009, 48, 2842.
[2] (a) Zen, J.-M.; Liu, S.-L.; Annamalai, M.-S. Angew. Chem., Int. Ed. 2003, 42, 577.
(b) Hirao, T.; Shiori, J.; Okahata, N. Bull. Chem. Soc. Jpn. 2004, 77, 1763.
(c) Herance, J.; Ferrer, B.; Bourdelande, J.; Marquet, J.; Garcia, H. Chemistry 2006, 12, 3890.
(d) Masahisa, O.; Han, N.; Munetaka, A. Royl. Soc. Chem. 2007, 8, 827.
[3] (a) Li, L.-T.; Ma, S.-M. J. Org. Chem. 2001, 21, 75(in Chinese). (李林涛, 麻生明, 有机化学, 2001, 21, 75.)
(b) Weng, J.-Q.; Liu, X.-H.; Zhang, G.-F.; Tan, C.-X.; Ding, C.-R.; Ou, X.-M. Chin. J. Org. Chem. 2011, 31, 374(in Chinese). (翁建全, 刘幸海, 张国富, 谭成侠, 丁成荣, 欧晓明, 有机化学, 2011, 31, 374.)
(c) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(d) Hering, T.; Hari, D. P.; Konig, B. J. Org. Chem. 2012, 77, 10347.
(e) Schroll, P.; Hari, D. P.; Konig, B. Chem. Open 2012, 1, 130.
(f) Huang, L.; Zhao, J. Chem. Commun. 2013, 49, 3751.
(g) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322.
(h) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387.
(i) Hari, D. P.; Hering, T.; Konig, B. Angew. Chem., Int. Ed. 2014, 53, 725.
(j) Liu, H.; Zhao, L.; Yuan, Y.; Xu, Z.; Chen, K.; Qiu, S.; Tan, H. ACS Catal. 2016, 6, 1732.
(h) Ren, X.; Guo, Q.; Chen, J.; Xie, H.; Xu, Q.; Lu, Z. Chemistry 2016, 22, 18695.
[4] (a) Tang, S.-S.; Zhang, N.; Zhu, J. Ind. Catal. 2005, 13, 21(in Chinese). (汤胜山, 张宁, 朱静, 工业催化, 2005, 13, 21.)
(b) Zhang, N.; Zhang, Y.-H.; Pan, X.-Y.; Fu, X.-Z.; Xu, Y.-J. Sci. China Chem. 2011, 41, 1097(in Chinese). (张楠, 张燕辉, 潘晓阳, 付贤智, 徐艺军, 中国科学:化学, 2011, 41, 1097.)
(b) Cui, E. T.; Lu, G. X. J. Phys. Chem. C 2013, 117, 26415.
(c) Meng, Q. Y.; Zhong, J. J.; Liu, Q.; Gao, X. W.; Zhang, H. H.; Lei, T.; Li, Z. J.; Feng, K.; Chen, B.; Tung, C. H.; Wu, L. Z. J. Am. Chem. Soc. 2013, 135, 19052.
(c) Kong, C.; Min, S. X.; Lu, G. X. ACS Catal. 2014, 4, 2763.
(d) Bhat, V. T.; Duspara, P. A.; Seo, S.; Abu Bakar, N. S. B.; Greaney, M. F. Chem. Commun. 2015, 51, 4383.
(e) Li, X. R.; Li, Y. Y.; Huang, Y. X.; Zhang, T.; Liu, Y. Z.; Yang, B.; He, C. X.; Zhou, X. C.; Zhang, J. M. Green Chem. 2017, 19, 2925.
(f) Liu, D.; Zhang, C.-H.; Han, N.; Du. M.-M.; Zhang, X.-L.; Zhao, P.-S.; Yang, P. Chin. J. Org. Chem. 2018, 38, 62(in Chinese). (张成慧, 韩楠, 杜萌萌, 张效露, 赵朋杉, 杨萍, 刘迪, 有机化学, 2018, 38, 62.)
[5] (a) Yuan, D.-Z.; Hhuang, B. Chin. J. Org. Chem. 2012, 32, 1368(in Chinese). (袁定重, 黄斌, 有机化学, 2012, 32, 1368.)
(b) Yin, J.; Liao, G.-Z.; Zhu, D.-Y.; Lu, P.; Li, L.-S. China Environ. Sci. 2016, 36, 735(in Chinese). (尹竞, 廖高祖, 朱冬韵, 卢平, 李来胜, 中国环境科学, 2016, 36, 735.)
(c) Dai, X.-W.; Wu, J.; Qi, X.-M.; Wu, Q.; Li, X. Res. Environ. Sci. 2014, 27, 827(in Chinese). (代学伟, 吴江, 齐雪梅, 吴强, 何平, 李忺, 环境科学研究, 2014, 27, 827.)
[6] Tang, T.; Wei, P.-F.; Li, L.; Yang, F.-K. Chem. Word 2018, 59, 144(in Chinese). (唐甜, 魏鹏飞, 李琳, 杨丰科, 化学世界, 2018, 59, 144.)
[7] Yadav, L.; Srivastava, V.; Yadav, A. Synlett 2013, 24, 465.
[8] (a) Ravelli, D.; Fagnoni, M. ChemCatChem 2012, 4, 169.
(b) Xiao, T.; Dong, X.; Tang, Y.; Zhou, L. Adv. Synth. Catal. 2012, 354, 3195.
(c) Hari, D. P.; Konig, B. Angew. Chem., Int. Ed. 2013, 52, 4734.
(d) Huang, L.; Zhao, J. RSC Adv. 2013, 3, 23377.
(e) Arbeloa, E. M.; Previtali, C. M.; Bertolotti, S. G. J. Lumin. 2016, 180, 369.
[9] Chu, Z.-Y.; Yuan, B.; Yan, Y.-N. J. Inorg. Mater. 2014, 29, 785(in Chinese). (楚增勇, 原博, 颜廷楠, 无机材料学报, 2014, 29, 785.)
[10] Sandrine, F.; Daniel, L.; Carlo, A. J. Phys. Chem. A 2008, 112, 7264.
[11] Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
[12] Fukuzumi, S.; Ohkubo, K. Org. Biomol. Chem. 2014, 12, 6059.
[13] (a) Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2013, 4, 355.
(b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[14] Hari, D. P.; Konig, B. Chem. Commun. 2014, 50, 6688.
[15] Srivastava, V.; Singh, P. P. RSC Adv. 2017, 7, 31377.
[16] Cheng, X.-K.; Hu, X.-G.; Lu, Z. Chin. J. Org. Chem. 2017, 37, 251(in Chinese). (程骁恺, 胡新根, 陆展, 有机化学, 2017, 37, 251.)
[17] Neumann, M.; Fuldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951.
[18] Pan, Y.; Kee, C. W.; Chen, L.; Tan, C. H. Green Chem. 2011, 13, 2682.
[19] Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C. H. Green Chem. 2011, 13, 3341.
[20] Liu, Q.; Li, Y. N.; Zhang, H. H.; Chen, B.; Tung, C. H.; Wu, L. Z. Chemistry 2012, 18, 620.
[21] Fu, W.; Guo, W.; Zou, G.; Xu, C. J. Fluorine Chem. 2012, 140, 88.
[22] Vila, C.; Bootwicha, T.; Rueping, M. ACS Catal. 2013, 3, 1676.
[23] Keshari, T.; Yadav, V. K.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2014, 16, 3986.
[24] Cantillo, D.; Frutos, O.; Rincon, J. A.; Mateos, C.; Kappe, C. O. Org. Lett. 2014, 16, 896.
[25] Li, X.; Gu, X.; Li, Y.; Li, P. ACS Catal. 2014, 4, 1897.
[26] Jadhav, S. D.; Bakshi, D.; Singh, A. J. Org. Chem. 2015, 80, 10187.
[27] Li, J.; Zhang, J.; Tan, H. B.; Wang, D. Z. Org. Lett. 2015, 17, 2522.
[28] Fuentes de Arriba, A. L.; Urbitsch, F.; Dixon, D. J. Chem. Commun. (Camb) 2016, 52, 14434.
[29] Schwarz, J.; König, B. Green Chem. 2016, 18, 4743.
[30] Wang, K.; Meng, L. G.; Wang, L. J. Org. Chem. 2016, 81, 7080.
[31] Zhang, N.; Quan, Z. J.; Zhang, Z.; Da, Y. X.; Wang, X. C. Chem. Commun (Camb). 2016, 52, 14234.
[32] Zhao, D.; Xie, Z. Angew. Chem., Int. Ed. 2016, 55, 3166.
[33] Meyer, A. U.; Slanina, T.; Yao, C. J.; König, B. ACS Catal. 2016, 6, 369.
[34] Ghosh, I.; BurkhardKonig Angew. Chem., Int. Ed. 2016, 55, 7676.
[35] Ghosh, I.; Marzo, L.; Das, A.; Shaikh, R.; König, B. Acc. Chem. Res. 2016, 49, 1566.
[36] Garrido, A. F.; Choubane, H.; Daaou, M.; Maestro, M. C.; Aleman, J. Chem. Commun. 2017, 53, 7764.
[37] Wu, L. L.; Tang, L.; Zhou, S. G.; Peng, Y. J.; He, X. D.; Guan, Z.; He, Y. H. Tetrahedron 2017, 73, 6471.
[38] Zhu, J.; Yuan, Y.; Wang, S.; Yao, Z.-J. ACS Omega 2017, 2, 4665.
[39] Graml, A.; Ghosh, I.; König, B. J. Org. Chem. 2017, 82, 3552.
[40] Pramanik, M. M. D.; Nagode, S. B.; Kant, R.; Rastogi, N. Org. Biomol. Chem. 2017, 15, 7369.
[41] Fan, X. Z.; Rong, J. W.; Wu, H. L.; Zhou, Q.; Deng, H. P.; Tan, J. D.; Xue, C. W.; Wu, L. Z.; Tao, H. R.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 1.
[42] Liu, H.; Feng, W.; Kee, C. W.; Zhao, Y.; Leow, D.; Pan, Y.; Tan, C. H. Green. Chem. 2010, 12, 953.
[43] Gu, X.; Li, X.; Chai, Y.; Yang, Q.; Li, P.; Yao, Y. Green Chem. 2013, 15, 357.
[44] Teo, Y. C.; Pan, Y.; Tan, C. H. ChemCatChem. 2013, 5, 235.
[45] Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275.
[46] Meyer, A. U.; Jäger, S.; Prasad, Hari. D.; König, B. Adv. Synth. Catal. 2015, 357, 2050.
[47] Yang, D.; Huang, B.; Wei, W.; Li, J.; Lin, G.; Liu, Y.; Ding, J.; Sun, P.; Wang, H. Green Chem. 2016, 18, 5630.
[48] Cai, S.; Xu, Y.; Chen, D.; Li, L.; Chen, Q.; Huang, M.; Weng, W. Org. Lett. 2016, 18, 2990.
[49] Zalesskiy, S. S.; Shlapakov, N. S.; Ananikov, V. P. Chem. Sci. 2016, 7, 6740.
[50] Huang, F.-Q.; Dong, X.; Qi, L.-W.; Zhang, B. Tetrahedron Lett. 2016, 57, 1600.
[51] Liu, X.; Qing, Z.; Cheng, P.; Zheng, X.; Zeng, J.; Xie, H. Molecules 2016, 21, 1690.
[52] Zhang, M. J.; Schroeder, G. M.; He, Y. H.; Guan, Z. RSC Adv. 2016, 6, 96693.
[53] Luo, K.; Chen, Y. Z.; Yang, W. C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
[54] Shaikh, R. S.; Düsel, S. J. S.; König, B. ACS Catal. 2016, 6, 8410.
[55] Ghosh, T.; Das, A.; König, B. Org. Biomol. Chem. 2017, 15, 2536.
[56] Guerrero-Corella, A.; Maria Martinez-Gualda, A.; Ahmadi, F.; Ming, E.; Fraile, A.; Aleman, J. Chem. Commun. (Camb). 2017, 53, 10463.
[57] Hong, B.; Lee, J.; Lee, A. Tetrahedron Lett. 2017, 58, 2809.
[58] Li, Y.; Wang, M.; Jiang, X. ACS Catal. 2017, 7, 7587.
[59] Yu, X.; Zhou, F.; Chen, J.; Xiao, W. Acta Chim. Sinica 2017, 75, 86(in Chinese). (喻晓叶, 周帆, 陈加荣, 肖文精, 化学学报, 2017, 75, 86.)
[60] Zhang, R.; Cai, Y.; Sun, D.; Xu, S.; Zhou, Q. Synlett 2017, 28, 1630.
[61] Zhang, Z.; Liu, F.; Bao, Z.; Su, B.; Xing, H.; Yang, Q.; Yang, Y.; Ren, Q. Synlett 2017, 28, 1116.
[62] Tibbetts, J. D.; Carbery, D. R.; Emanuelsson, E. A. C. ACS Sustainable Chem. Eng. 2017, 5, 9826.
[63] Cui, H.; Wei, W.; Yang, D.; Zhang, Y.; Zhao, H.; Wang, L.; Wang, H. Green Chem. 2017, 19, 3520.
[64] Bottecchia, C.; Rubens, M.; Gunnoo, S. B.; Hessel, V.; Madder, A.; Noel, T. Angew. Chem., Int. Ed. 2017, 56, 12702.
[65] Zhu, J.; Cui, W. C.; Wang, S.; Yao, Z. J. Org. Lett. 2018, 20, 3174.
[66] Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y. N.; Chen, J. R.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 2265.
[67] Gu, L.; Jin, C.; Liu, J. Green Chem. 2015, 17, 3733.
[68] Majek, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2015, 54, 2270.
[69] Tankam, T.; Poochampa, K.; Vilaivan, T.; Sukwattanasinitt M.; Wacharasindhu, S. Tetrahedron 2016, 72, 788.
[70] Sun, J. G.; Yang, H.; Li, P.; Zhang, B. Org. Lett. 2016, 18, 5114.
[71] Kalaitzakis, D.; Montagnon, T.; Alexopoulou, I.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2012, 51, 8868.
[72] Gong, Q.; Luo, H.; Cao, D.; Zhang, H.; Wang, W.; Zhou, X. B. Korean. Chem. Soc. 2012, 33, 1945.
[73] Chen, L.; Chao, C. S.; Pan, Y.; Dong, S.; Teo, Y. C.; Wang, J.; Tan. C. H. Org. Biomol. Chem. 2013, 11, 5922.
[74] Vila, C.; Lau, J.; Rueping, M. Beilstein J. Org. Chem. 2014, 10, 1233.
[75] Wang, L.; Ma, Z. G.; Wei, X. J.; Meng, Q. Y.; Yang, D. T.; Du, S. F.; Chen, Z. F.; Wu, L. Z.; Liu, Q. Green Chem. 2014, 16, 3752.
[76] Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z. W.; Zhou, L. Green Chem. 2014, 16, 2418.
[77] Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643.
[78] Yoshioka, E.; Jichu, T.; Fukazawa, T.; Nagai, T.; Takemoto, Y.; Kohtani, S.; Miyabe, H. Synlett 2014, 26, 265.
[79] Liang, Z.; Xu, S.; Tian, W.; Zhang, R. J. Org. Chem. 2015, 11, 425.
[80] Shen, Z. C.; Yang, P.; Tang, Y. J. Org. Chem. 2015, 81, 309.
[81] Davies, J.; Booth, S. G.; Essafi, S.; Dryfe, R. A. W.; Leonori, D. Angew. Chem., Int. Ed. 2015, 54, 14017.
[82] Yadav, A. K.; Yadav, L. D. S. Green Chem. 2015, 17, 3515.
[83] Yadav, L.; Kapoorr, R.; Singh, S.; Tripathi, S. Synlett 2015,26, 1201.
[84] Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. (Camb.) 2015, 51, 7520.
[85] Yang, Z.; Li, H.; Zhang, L.; Zhang, M. T.; Cheng, J. P.; Luo, S. Chemistry 2015, 21, 14723.
[86] Yadav, A. K.; Yadav, L. D. S. Green Chem. 2016, 18, 4240.
[87] Kovvuri, J.; Nagaraju, B.; Kamal, A.; Srivastava, A. K. ACS Comb. Sci. 2016, 18, 644.
[88] Quint, V.; Morlet-Savary, F.; Lohier, J. F.; Lalevee, J.; Gaumont, A. C.; Lakhdar, S. J. Am. Chem. Soc. 2016, 138, 7436.
[89] Rohokale, R. S.; Koenig, B.; Dhavale, D. D. J. Org. Chem. 2016, 81, 7121.
[90] Das, A.; Ghosh, I.; König, B. Chem. Commun. 2016, 52, 8695.
[91] Borpatra, P. J.; Deb, M. L.; Baruah, P. K. Tetrahedron Lett 2017, 58, 4006.
[92] Huang, M.-H.; Zhu, Y.-L.; Hao, W.-J.; Wang, A.-F.; Wang, D.-C.; Liu, F.; Wei, P.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2017, 359, 2229.
[93] Liu, D.; Chen, J. Q.; Wang, X. Z.; Xu, P. F. Adv. Synth. Catal. 2017, 359, 2773.
[94] Jin, C.; Su, L.; Ma, D.; Cheng, M. New J. Chem. 2017, 41, 14053.
[95] Wei, W.; Cui, H.; Yang, D.; Yue, H.; He, C.; Zhang, Y.; Wang, H. Green Chem. 2017, 19, 5608.
[96] Mondal, R. R.; Khamarui, S.; Maiti, D. K. Org. Lett. 2017, 19, 5964.
[97] Wu, L. L.; Yang, G. H.; Guan, Z.; He, Y. H. Tetrahedron 2017, 73, 1854.
[98] Sun, D.; Yin, K.; Zhang, R. Chem. Commun. (Camb.) 2018, 54, 1335.
[99] Diao, P.; Ge, Y.; zhang, W.; Xu, C.; Zhang, N.; Guo, C. Tetrahedron Lett. 2018, 59, 767.
[100] Alberti, M. N.; Vougioukalakis, G. C.; Orfanopoulos, M. J. Org. Chem. 2009, 74, 7274.
[101] Griesbeck, A. G.; Steinwascher, J.; Reckenthäler, M.; Uhlig, J. Res. Chem. Intermed. 2012, 39, 33.
[102] Li, J.; Wang, H.; Liu, L.; Sun, J. RSC Adv. 2014, 4, 49974.
[103] Yadav, A. K.; Srivastava, V. P.; Yadav, L. D. S. RSC Adv. 2014, 4, 4181.
[104] Liu, X.; Cong, T.; Liu, P.; Sun, P. J. Org. Chem. 2016, 81, 7256.
[105] Devari, S.; Rizvi, M. A.; Shah, B. A. Tetrahedron Lett. 2016, 57, 3294.
[106] Cheng, X.; Yang, B.; Hu, X.; Xu, Q.; Lu, Z. Chemistry 2016, 22, 17566.
[107] Jin, Y.; Ou, L.; Yang, H.; Fu, H. J Am. Chem. Soc. 2017, 139, 14237.
[108] Yue, H.; Nan, G. Synlett 2018, 29, 1340.
[109] Sahoo, M. K.; Jaiswal, G.; Rana. J.; Balaraman, E. Chemistry 2017, 23, 14167.
[110] Kee, C. W.; Chan, K. M.; Wong, M. W.; Tan, C. H. Asian J. Org. Chem. 2014, 3, 536.
[111] Yang, X. J.; Chen, B.; Zheng, L. Q.; Wu, L. Z.; Tung, C. H. Green Chem. 2014, 16, 1082.
[112] Yang, D. T.; Meng, Q. Y.; Zhong, J. J.; Xiang, M.; Liu, Q.; Wu, L. Z. Eur. J.Org. Chem. 2013, 2013, 7528.
[113] Liu, Z.; Zhang, Y.; Cai, Z.; Sun, H.; Cheng, X. Adv. Synth. Catal. 2015, 357, 589.
[114] Majek, M.; Filace, F.; Wangelin, A. J. Chemistry 2015, 21, 4518.
[115] Yi, H.; Niu, L. B.; Wang, S. C.; Liu, T. Y.; Singh, A. K.; Lei, A. W. Org. Lett. 2016, 19, 122.
[116] Tucker, B. S.; Coughlin, M. L.; Figg, C. A.; Sumerlin, B. S. ACS Macro Lett. 2017, 6, 452.