Chinese Journal of Organic Chemistry >
Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones
Received date: 2023-11-07
Revised date: 2023-12-11
Online published: 2023-12-21
Supported by
Shanghai Rising-Star Program(22QB1402800)
2,7-Diaryl substituted fluorenes and fluorenones are widely used in fields of organic semiconductor, chemosensor, and metallocene catalysis. Traditional synthesis methods can not meet the requirements of flexible molecular structures and regulation of diverse properties. Aryl-aryl cross coupling reactions based on the catalysis of Pd and Ni complexes have become efficient methods for the preparation of 2,7-diaryl substituted fluorenes and fluorenones. Various types of metal catalysts with phosphine ligands and N-heterocyclic carbene ligands have been applied. The synthetic methods of 2,7-diaryl substituted fluorenones and 2,7-diaryl substituted fluorenes with or without 9-substitutions, and the conditions for the application of Pd and Ni complexes are reviewed. The challenges of various synthetic methods at present are summarized and a brief outlook on possible solutions is provided.
Key words： biaryl; fluorene; fluorenone; luminescent material; metallocene
Yongqing Li , Yuqing Peng , Yucai Cao , Guiping Cao . Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1494 -1505 . DOI: 10.6023/cjoc202311008
| [1] | Rizzo, F.; Polo, F.; Bottaro, G.; Fantacci, S.; Antonello, S.; Armelao, L.; Quici, S.; Maran, F. J. Am. Chem. Soc. 2017, 139, 2060. |
| [2] | Du, X.; Xu, F.; Yuan, M.-S.; Xue, P.; Zhao, L.; Wang, D.-E.; Wang, W.; Tu, Q.; Chen, S.-W.; Wang, J. J. Mater. Chem. C 2016, 4, 8724. |
| [3] | Huo, Y. P.; Fang, X. M.; Huang, B. H.; Zhang, K.; Nie, X. L.; Zeng, H. P. Chin. J. Org. Chem. 2012, 32, 1169 (in Chinese). |
| [3] | ( 霍延平, 方小明, 黄宝华, 张焜, 聂晓李, 曾和平, 有机化学, 2012, 32, 1169.) |
| [4] | Liu, D.; De, J.; Gao, H.; Ma, S.; Ou, Q.; Li, S.; Qin, Z.; Dong, H.; Liao, Q.; Xu, B.; Peng, Q.; Shuai, Z.; Tian, W.; Fu, H.; Zhang, X.; Zhen, Y.; Hu, W. J. Am. Chem. Soc. 2020, 142, 6332. |
| [5] | Kobin, B.; Bianchi, F.; Halm, S.; Leistner, J.; Blumstengel, S.; Henneberger, F.; Hecht, S. Adv. Funct. Mater. 2014, 24, 7717. |
| [6] | Lin, H.-Y.; Sher, C.-W.; Lin, C.-H.; Tu, H.-H.; Chen, X. Y.; Lai, Y.-C.; Lin, C.-C.; Chen, H.-M.; Yu, P.; Meng, H.-F.; Chi, G.-C.; Honjo, K.; Chen, T.-M.; Kuo, H.-C. ACS Appl. Mater. Inter. 2017, 9, 35279. |
| [7] | Watanabe, K.; Sakamoto, T.; Taguchi, M.; Fujiki, M.; Nakano, T. Chem. Commun. 2011, 47, 10996. |
| [8] | Kim, Y. G.; Shaik, B.; Jang, Y. J.; Park, S. Y.; Kim, J. Y.; Lee, S.-G. J. Nanosci. Nanotechnol. 2016, 16, 2979. |
| [9] | Liu, D.; Liao, Q.; Peng, Q.; Gao, H.; Sun, Q.; De, J.; Gao, C.; Miao, Z.; Qin, Z.; Yang, J.; Fu, H.; Shuai, Z.; Dong, H.; Hu, W. Angew. Chem., Int. Ed. 2021, 60, 20274. |
| [10] | Liu, D.; Wu, X.; Gao, C.; Li, C.; Zheng, Y.; Li, Y.; Xie, Z.; Ji, D.; Liu, X.; Zhang, X.; Li, L.; Peng, Q.; Hu, W.; Dong, H. Angew. Chem., Int. Ed. 2022, 61, e202200791. |
| [11] | Locklin, J.; Ling, M. M.; Sung, A.; Roberts, M. E.; Bao, Z. Adv. Mater. 2006, 18, 2989. |
| [12] | Vaitukaityte, D.; Magomedov, A.; Rakstys, K.; Kwiatkowski, S.; Kamarauskas, E.; Jankauskas, V.; Rousseau, J.; Getautis, V. RSC Adv. 2023, 13, 26933. |
| [13] | Krucaite, G.; Beresneviciute, R.; Tavgeniene, D.; Grigalevicius, S.; Zhang, B.; Gruodis, A.; Chernyakova, K.; Karpicz, R. Opt. Mater. 2021, 119, 111345. |
| [14] | Du, X.; Su, H.; Zhao, L.; Xing, X.; Wang, B.; Qiu, D.; Wang, J.; Yuan, M.-S. Mater. Chem. Front. 2021, 5, 7508. |
| [15] | Duan, Y.; Ju, C.; Yang, G.; Fron, E.; Coutino-Gonzalez, E.; Semin, S.; Fan, C.; Balok, R. S.; Cremers, J.; Tinnemans, P.; Feng, Y.; Li, Y.; Hofkens, J.; Rowan, A. E.; Rasing, T.; Xu, J. Adv. Funct. Mater. 2016, 26, 8968. |
| [16] | Li, X.; Guan, J.; Hao, C.; Yu, Z.; Zheng, J. Chin. J. Chem. Phys. 2021, 34, 867. |
| [17] | Turelli, M.; Ciofini, I.; Wang, Q.; Ottochian, A.; Labat, F.; Adamo, C. Phys. Chem. Chem. Phys. 2023, 25, 17769. |
| [18] | Cheng, J.; Liu, Z.; Wang, D.; Chen, K.; You, Y.; Zhou, X. Appl. Organomet. Chem. 2019, 33, e5168. |
| [19] | Han, Y.; Zhao, J.; Yang, H.; Huang, X.; Zhou, X.; Hui, T.; Yan, J. J. Mol. Struct. 2020, 1217, 128395. |
| [20] | Tahir Waseem, M.; Muhammad Junaid, H.; Gul, H.; Ali Khan, Z.; Yu, C.; Anjum Shahzad, S. J. Photochem. Photobiol., A 2022, 425, 113660. |
| [21] | Yemam, H. A.; Mahl, A.; Tinkham, J. S.; Koubek, J. T.; Greife, U.; Sellinger, A. Chem.-Eur. J. 2017, 23, 8921. |
| [22] | Allushi, A.; Bakvand, P. M.; Jannasch, P. Macromolecules 2023, 56, 1165. |
| [23] | Pan, D.; Olsson, J. S.; Jannasch, P. ACS Appl. Energy Mater. 2022, 5, 981. |
| [24] | Ghosh, S.; Banerjee, S. J. Membr. Sci. 2014, 470, 535. |
| [25] | Sprick, R. S.; Bonillo, B.; Clowes, R.; Guiglion, P.; Brownbill, N. J.; Slater, B. J.; Blanc, F.; Zwijnenburg, M. A.; Adams, D. J.; Cooper, A. I. Angew. Chem., Int. Ed. 2016, 55, 1792. |
| [26] | Alt, H. G.; Zenk, R. J. Organomet. Chem. 1996, 522, 39. |
| [27] | Esteb, J. J.; Bergeron, M.; Dormady, C. N.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 2003, 675, 97. |
| [28] | Li, B.; Zhou, J.; Bai, F.; Xing, Y. Dyes Pigm. 2020, 172, 107862. |
| [29] | Staehler, C.; Grunenberg, L.; Terban, M. W.; Browne, W. R.; Doellerer, D.; Kathan, M.; Etter, M.; Lotsch, B. V.; Feringa, B. L.; Krause, S. Chem. Sci. 2022, 13, 8253. |
| [30] | Barnett, M. D.; Daub, G. H.; Hayes, F. N.; Ott, D. G. J. Am. Chem. Soc. 1959, 81, 4583. |
| [31] | Sakamoto, T.; Fukuda, Y.; Sato, S.-I.; Nakano, T. Angew. Chem., Int. Ed. 2009, 48, 9308. |
| [32] | Watanabe, K.; Sakamoto, T.; Nakano, T. Chirality 2011, 23, E28. |
| [33] | Mohammadkhanni, A.; Bazgir, A. Mol. Catal. 2018, 447, 28. |
| [34] | Li, H. B.; Seechurn, C.; Colacot, T. J. ACS Catal. 2012, 2, 1147. |
| [35] | Seechurn, C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062. |
| [36] | Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. |
| [37] | Colacot, T. J. Platinum Met. Rev. 2011, 55, 84. |
| [38] | Ni, C.; Shen, A.; Cao, Y. C.; Ye, X. F. Chin. J. Org. Chem. 2014, 34, 278 (in Chinese). |
| [38] | ( 倪晨, 沈安, 曹育才, 叶晓峰, 有机化学, 2014, 34, 278.) |
| [39] | Li, Y. Q.; Cao, Y. C.; Ye, X. F.; Zhou, H. Chin. J. Org. Chem. 2011, 31, 1538 (in Chinese). |
| [39] | ( 李永清, 曹育才, 叶晓峰, 周慧, 有机化学, 2011, 31, 1538.) |
| [40] | Bolliger, J. L.; Frech, C. M. Adv. Synth. Catal. 2010, 352, 1075. |
| [41] | Groombridge, B. J.; Goldup, S. M.; Larrosa, I. Chem. Commun. 2015, 51, 3832. |
| [42] | Zhang, Z.; Ji, H. Y.; Fu, X. L.; Yang, Y.; Xue, Y. R.; Gao, G. H. Chin. Chem. Lett. 2009, 20, 927. |
| [43] | Wen, X.; Wang, J.; He, L.; Wei, B.; Xie, Y. J. Carbohydr. Chem. 2022, 41, 369. |
| [44] | Xie, Q.; Li, J.; Wen, X.; Huang, Y.; Hu, Y.; Huang, Q.; Xu, G.; Xie, Y.; Zhou, Z. Carbohydr. Res. 2022, 512, 108516. |
| [45] | Destri, S.; Pasini, M.; Botta, C.; Porzio, W.; Bertini, F.; Marchio, L. J. Mater. Chem. 2002, 12, 924. |
| [46] | Kotaka, H.; Konishi, G.-I.; Mizuno, K. Tetrahedron Lett. 2010, 51, 181. |
| [47] | Wei, R. B.; Liu, Y.; Guo, J. J.; Liu, B.; Zhang, D. W. Chin. J. Org. Chem. 2008, 28, 390 (in Chinese). |
| [47] | ( 魏荣宝, 刘洋, 郭金晶, 刘博, 张大为, 有机化学, 2008, 28, 390.) |
| [48] | Qin, C.; Liu, W.; Nie, Y.; Gao, Y.; Miao, J.; Li, T.; Jiang, X. Chin. J. Org. Chem. 2020, 40, 2232 (in Chinese). |
| [48] | ( 秦成远, 刘威, 聂永, 高迎, 苗金玲, 李天瑞, 蒋绪川, 有机化学, 2020, 40, 2232.) |
| [49] | Sakamoto, T.; Watanabe, K.; Shichibu, Y.; Konishi, K.; Sato, S.-I.; Nakano, T. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 945. |
| [50] | Ju, C.; Li, X.; Yang, G.; Yuan, C.; Semin, S.; Feng, Y.; Rasing, T.; Xu, J. Dyes Pigm. 2019, 166, 272. |
| [51] | Thirion, D.; Poriel, C.; Metivier, R.; Rault-Berthelot, J.; Barriere, F.; Jeannin, O. Chem.-Eur. J. 2011, 17, 10272. |
| [52] | Xu, J.; Semin, S.; Niedzialek, D.; Kouwer, P. H. J.; Fron, E.; Coutino, E.; Savoini, M.; Li, Y.; Hofkens, J.; Uji-I, H.; Beljonne, D.; Rasing, T.; Rowan, A. E. Adv. Mater. 2013, 25, 2084. |
| [53] | Liu, Y.-W.; Huang, J.; Tan, J.-H.; Zeng, Y.; Ding, Q.; Xiang, X.-W.; Liu, Y.-J.; Zhang, H.-L. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2373. |
| [54] | Qiu, S.; Zhang, Y.; Huang, X.; Bao, L.; Hong, Y.; Zeng, Z.; Wu, J. Org. Lett. 2016, 18, 6018. |
| [55] | Dmochowska, E.; Bombalska, A.; Kula, P. Liq. Cryst. 2020, 47, 17. |
| [56] | Hadizad, T.; Zhang, J.; Wang, Z. Y.; Gorjanc, T. C.; Py, C. Org. Lett. 2005, 7, 795. |
| [57] | Kuhnert, N.; Patel, C.; Jami, F. Tetrahedron Lett. 2005, 46, 7575. |
| [58] | Salunke, A. K.; Ghosh, A.; Banerjee, S. J. Appl. Polym. Sci. 2007, 106, 664. |
| [59] | Holloway, L. R.; Bogie, P. M.; Lyon, Y.; Ngai, C.; Miller, T. F.; Julian, R. R.; Hooley, R. J. J. Am. Chem. Soc. 2018, 140, 8078. |
| [60] | Zhou, Z. G.; Zhao, Y.; Zhen, H. Y.; Lin, Z. H.; Ling, Q. D. Appl. Organomet. Chem. 2016, 30, 924. |
| [61] | Zhou, Z.; Yuan, Y.; Xie, Y.; Li, M. Catal. Lett. 2018, 148, 2696. |
| [62] | Zhou, Z.; Li, M.; Liu, G.; Xu, G.; Xue, J. Appl. Organomet. Chem. 2019, 33, e4942. |
| [63] | Zhou, Z.; Xie, Q.; Zhou, X.; Yuan, Y.; Pan, Y.; Lu, D.; Du, Z.; Xue, J. Carbohydr. Res. 2020, 496, 108079. |
| [64] | Zhou, Z.; Xie, Q.; Li, J.; Yuan, Y.; Liu, Y.; Liu, Y.; Lu, D.; Xie, Y. Catal. Lett. 2022, 152, 838. |
| [65] | Wu, Y.; Dou, Z. J.; Wu, C. M.; Chen, H. B.; Zhang, Z. M.; Wang, X. X.; Yin, Z. Q.; Song, X.; He, C. L.; Yue, G. Z. Chin. J. Org. Chem. 2018, 38, 2896 (in Chinese). |
| [65] | ( 吴瑶, 豆正杰, 吴彩梅, 陈华保, 张祖民, 王显祥, 殷中琼, 宋旭, 贺常亮, 乐贵洲, 有机化学, 2018, 38, 2896.) |
| [66] | Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674. |
| [67] | Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440. |
| [68] | Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461. |
| [69] | Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151. |
| [70] | Valente, C.; ?alimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314. |
| [71] | Biffis, A.; Centomo, P.; Del Zotto, A.; Zeccal, M. Chem. Rev. 2018, 118, 2249. |
| [72] | Krishnaraj, P.; Reddy, S. R. New J. Chem. 2023, 47, 974. |
| [73] | Polshettiwar, V.; Decottignies, A.; Len, C.; Fihri, A. ChemSusChem 2010, 3, 502. |
| [74] | Hooshmand, S. E.; Heidari, B.; Sedghi, R.; Varma, R. S. Green Chem. 2019, 21, 381. |
| [75] | Xu, P.; Duan, X. H. Chin. J. Org. Chem. 2019, 39, 3315 (in Chinese). |
| [75] | ( 徐鹏, 段新红, 有机化学, 2019, 39, 3315.) |
| [76] | Jose, D. E.; Kanchana, U. S.; Mathew, T. V.; Anilkumar, G. J. Organomet. Chem. 2020, 927, 121538. |
| [77] | Kelley, C. J.; Ghiorghis, A.; Kauffman, J. M. J. Chem. Res., Synop. 1997, 446. |
| [78] | Biswas, A.; Bains, A. K.; Adhikari, D. Catal. Sci. Technol. 2022, 12, 4211. |
| [79] | Sharma, R.; Mondal, A.; Samanta, A.; Srimani, D. Catal. Sci. Technol. 2023, 13, 611. |
| [80] | Mondal, A.; Sharma, R.; Pal, D.; Srimani, D. Chem. Commun. 2021, 57, 10363. |
| [81] | Liu, Y.; Zhang, Y.; Wu, X.; Lan, Q.; Chen, C.; Liu, S.; Chi, Z.; Jiang, L.; Chen, X.; Xu, J. J. Mater. Chem. C 2014, 2, 1068. |
| [82] | Peng, Z.; Tao, S.; Zhang, X.; Tang, J.; Lee, C. S.; Lee, S.-T. J. Phys. Chem. C 2008, 112, 2165. |
| [83] | Huang, W. Y.; Chang, M. Y.; Han, Y. K.; Huang, P. T. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5872. |
| [84] | Liu, J. J.; Qin, H.; Bar, X. W. Acta Polym. Sin. 2011, 42, 217 (in Chinese). |
| [84] | ( 刘进军, 秦红, 巴信武, 高分子学报, 2011, 42, 217.) |
| [85] | Kumar, S.; Karthik, D.; Thomas, K. R. J.; Hundal, M. S. Tetrahedron Lett. 2014, 55, 1931. |
| [86] | Kotha, S.; Ali, R. J. Chem. Sci. 2019, 131, 1. |
| [87] | Asai, K.; Konishi, G.-I.; Sumi, K.; Kawauchi, S. Polym. Chem. 2010, 1, 321. |
| [88] | Liu, L. L.; Song, W. L.; Zhang, Z. Y.; Sun, P. F.; Lu, X. M.; Fan, Q. L.; Huang, W. Acta Polym. Sin. 2011, 42, 724 (in Chinese). |
| [88] | ( 柳露林, 宋文利, 张志勇, 孙鹏飞, 卢晓梅, 范曲立, 黄维, 高分子学报, 2011, 42, 724.) |
| [89] | Li, L.; Wang, Z.; Chen, Q.; Zhou, X.; yang, T.; Zhao, Q.; Huang, W. J. Solid State Chem. 2015, 231, 47. |
| [90] | Jung, S. H.; Suh, D. H.; Cho, H. N. Polym. Bull. 2003, 50, 251. |
| [91] | Grisorio, R.; Mastrorilli, P.; Suranna, G. P. Polym. Chem. 2014, 5, 4304. |
| [92] | Liu, Z.-P.; Li, X.; Jiang, J.; Zhao, Y.-Y.; Zhao, X.-H.; Chen, H.-B. Chin. J. Lumin. 2013, 34, 579 (in Chinese). |
| [92] | ( 刘志鹏, 李星, 江晶, 赵亚云, 赵秀华, 陈红兵, 发光学报, 2013, 34, 579.) |
| [93] | Tao, S. L.; Zhou, Y. C.; Lee, C. S.; Zhang, X. H.; Lee, S. T. Chem. Mater. 2010, 22, 2138. |
| [94] | Han, Q.; Su, Q.; Tang, L.; Feng, J.; Lu, P.; Wang, Y. J. Phys. Chem. C 2010, 114, 18702. |
| [95] | Wang, Z.; Shao, H.; Ye, J.; Zhang, L.; Lu, P. Adv. Funct. Mater. 2007, 17, 253. |
| [96] | Zhao, Y.-Y.; Liu, Z.-P.; Zhao, X.-H.; Zhang, J.; Li, X. Chin. J. Lumin. 2014, 35, 156 (in Chinese). |
| [96] | ( 赵亚云, 刘志鹏, 赵秀华, 张洁, 李星, 发光学报, 2014, 35, 156.) |
| [97] | Lee, H. W.; Kim, H. J.; Kim, Y. S.; Kim, J.; Lee, S. E.; Lee, H. W.; Kim, Y. K.; Yoon, S. S. Displays 2015, 39, 1. |
| [98] | Dubey, D. K.; Krucaite, G.; Swayamprabha, S. S.; Yadav, R. A. K.; Blazevicius, D.; Tagare, J.; Chavhan, S.; Hsueh, T.-C.; Vaidyanathan, S.; Grigalevicius, S.; Jou, J.-H. Org. Electron. 2020, 79, 105633. |
/
| 〈 |
|
〉 |
