Citation: Teng Qiaoling, Xu Lulu, Cheng Dongping, Xu Xiaoliang. Synthesis of 10-Phenanthrenol Derivatives via Visible Light Catalyzed Itramolecular Cycloaromatization[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4258-4266. doi: 10.6023/cjoc202005077 shu

Synthesis of 10-Phenanthrenol Derivatives via Visible Light Catalyzed Itramolecular Cycloaromatization

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b.
College of Pharmaceutical, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Cheng Dongping, chengdp@zjut.edu.cn Xu Xiaoliang, xuxiaoliang@zjut.edu.cn
Received Date: 28 May 2020
Revised Date: 21 July 2020
Available Online: 5 August 2020
Fund Project: the National Natural Science Foundation of China 21602197the Zhejiang Provincial Natural Science Foundation LY18B020018Project supported by the Zhejiang Provincial Natural Science Foundation (Nos. LY18B020018, LY15B020004) and the National Natural Science Foundation of China (No. 21602197)the Zhejiang Provincial Natural Science Foundation LY15B020004

Figures(2)

Phenanthrene derivatives play an important role in pharmaceutical chemistry and material science. Due to its advantages of green, mild reaction conditions and great application potential, visible light catalysis has become a powerful tool in organic synthesis. In this paper, under the catalysis of photocatalyst Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆, a series of 10-phenanthrenol derivatives were synthesized from 2-arylbenzoyl acetate derivatives in moderate to good yields through intramolecular cycloaromatization. In addition, the plausible reaction mechanism was also proposed.
- visible-light photocatalysis,
- radical reaction,
- intramolecular cycloaromatization,
- phenanthrenols
1. [1]
  (a) Floyd, A. J.; Dyke, S. F.; Ward, S. E. Chem. Rev. 1976, 76, 509.
  (b) Kovács, A.; Vasas, A.; Hohmann, J. Phytochemistry 2008, 69, 1084.
  (c) Narita, A.; Wang, X.; Feng, X.; Mullen, K. Chem. Soc. Rev. 2015, 44, 6616.
2. [2]
  (a) De Alvarenga, M. A.; Gottlieb, O. R.; Magalhaes, M. T. Phytochemistry 1976, 15, 844.
  (b) Pettit, G. R.; Singh, S. B.; Niven, M. L.; Schmidt, J. M. Can. J. Chem. 1988, 66, 406.
  (c) Cragg, G. M.; Newman, D. J. J. Nat. Prod. 2004, 67, 232.
3. [3]
  (a) Huffman, C. W.; Traxler, J. T.; Krbechek, L. O.; Riter, R. R.; Wagner, R. G. J. Med. Chem. 1971, 14, 90.
  (b) Colwell, W. T.; Brown, V.; Christie, P.; Lange, J.; Reece, C.; Yamamoto, K.; Henry, D. W. J. Med. Chem. 1972, 15, 771.
4. [4]
  Matsuda, H.; Morikawa, T.; Xie, H.; Yoshikawa, M. Planta Med. 2004, 70, 847. doi: 10.1055/s-2004-827234
5. [5]
  (a) Fisch, M. H.; Flick, B. H.; Arditti, J. Phytochemistry 1973, 12, 437.
  (b) Yamaki, M.; Bai, L.; Inoue, K.; Takagi, S. Phytochemistry 1989, 28, 3503.
6. [6]
  (a) Mitsuhashi, R.; Suzuki, Y.; Yamanari, Y.; Mitamura, H.; Kambe, T.; Ikeda, N.; Okamoto, H.; Fujiwara, A.; Yamaji, M.; Kawasaki, N.; Maniwa, Y.; Kubozono, Y. Nature 2010, 464, 76.
  (b) Lewis, F. D.; Burch, E. L. J. Phys. Chem. 1996, 100, 4055.
  (c) Machado, A. M.; Munaro, M.; Martins, T. D.; Dávila, L. Y. A.; Giro, R.; Caldas, M. J.; Atvars, T. D. Z.; Akcelrud, L. C. Macromolecules 2006, 39, 3398.
  (d) Matsuo, Y.; Sato, Y.; Hashiguchi, M.; Matsuo, K.; Nakamura, E. Adv. Funct. Mater. 2009, 19, 2224.
7. [7]
  (a) Yadav, A. K.; Ila, J.; Junjappa, H. Eur. J. Org. Chem. 2010, 2010, 338.
  (b) Gupta, V.; Rao, V. U. B.; Das, T.; Vanka, K.; Singh, R. P. J. Org. Chem. 2016, 81, 5663.
  (c) Gupta, V.; Pandey, S. K.; Singh, R. P. Org. Biomol. Chem. 2018, 16, 7134.
8. [8]
  (a) Bogert, M. T. Science 1933, 77, 289.
  (b) Floyd, A. J.; Dyke, S. F.; Ward, S. E. Chem. Rev. 1976, 76, 509.
9. [9]
  (a) Almeida, J. F.; Castedo, L.; Fernández, D.; Neo, A. G.; Romero, V.; Tojo, G. Org. Lett. 2003, 5, 4939.
  (b) Kang, Y.; Wang, T.; Liang, Y.; Zhang, Y.; Wang, R.; Zhang, Z. RSC Adv. 2017, 7, 44333.
  (c) Kang, T.; Zhang, W.; Wang, T.; Liang, Y.; Zhang, Z. J. Org. Chem. 2019, 84, 12387.
  (d) Neo, A. G.; López, C.; Romero, V.; Antelo, B.; Delamano, J.; Pérez, A.; Fernandez, D.; Almeida, J. E.; Castedo, L.; Tojo, G. J. Org. Chem. 2010, 75, 6764.
10. [10]
  (a) Mallory, F. B.; Wood, C. S.; Gordon, J. T. J. Am. Chem. Soc. 1964, 86, 3094.
  (b) Wood, C. S.; Mallory, F. B. J. Org. Chem. 1964, 29, 3373.
  (c) Matsushima, T.; Kobayashi, S.; Watanabe, S. J. Org. Chem. 2016, 81, 7799.
11. [11]
  Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185. doi: 10.1016/S0040-4039(02)00505-1
12. [12]
  Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 5714. doi: 10.1002/anie.201201374
13. [13]
  (a) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405.
  (b) McMurry J. E. Chem. Rev. 1989, 89, 1513.
  (c) Gies, A. E.; Pfeffer, M. J. Org. Chem. 1999, 64, 3650.
14. [14]
  (a) Iuliano, A.; Piccioli, P.; Fabbri, D. Org. Lett. 2004, 6, 3711.
  (b) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006, 45, 2664.
  (c) McAtee, C. C.; Riehl, P. S.; Schindler, C. S. J. Am. Chem. Soc. 2017, 139, 2960.
15. [15]
  Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 6, 7536.
  (b) Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 6557.
  (c) Yan, J.; Yoshikai, N. Org. Lett. 2017, 19, 6630.
16. [16]
  Gou, B.; Yang, H.; Sun, H.; Chen, J.; Wu, J.; Zhou, L. Org. Lett. 2019, 21, 80.
  (b) Yao, T.; Zhang, H.; Zhao, Y. Org. Lett. 2016, 18, 2532.
  (c) Song, J.; Wang, S.; Sun, H.; Fan, Y.; Xiao, K.; Qian, Y. Org. Biomol. Chem. 2019, 17, 3328.
  (d) Iwasaki, M.; Araki, Y.; Nishihara, Y. J. Org. Chem. 2017, 82, 6242.
17. [17]
  Liu, Y.; Chen, L.; Wang, Z.; Liu, P.; Liu, Y.; Dai, B. J. Org. Chem. 2019, 84, 204. doi: 10.1021/acs.joc.8b02605
18. [18]
  (a) Liu, W.; Zhang, Y.; Guo, H. J. Org. Chem. 2018, 83, 10518.
  (b) Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511.
19. [19]
  (a) Xuan, J.; Xiao, W. Angew. Chem., Int. Ed. 2012, 51, 6828.
  (b) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
  (c) Dai, C.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2011, 3, 140.
  (d) Uygur, M.; Danelzik, T.; Mancheño, O. G. Chem. Commun. 2019, 55, 2980.
  (e) Chen, J.; Cen, J.; Xu, X.; Li, X. Catal. Sci. Technol. 2016, 6, 349.
  (f) Chen, Y.; Lu, L.; Yu, D.; Zhu, C.; Xiao, W. Sci. China Chem. 2019, 62, 24.
  (g) Goddard, J. P.; Ollivier, C.; Fensterbank, L. Acc. Chem. Res. 2016, 49, 1924.
  (h) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
  (i) Zhang, H.; Lei, A. Asian J. Org. Chem. 2018, 7, 1164.
  (j) Yu, X.; Zhao, Q.; Chen, J.; Xiao, W.; Chen, J. Acc. Chem Res. 2020, 53, 1066.
  (k) Yang, X.; Guo, J.; Xiao, H.; Feng, K.; Chen, B.; Tung, C.; Wu, L. Angew. Chem. Int. Ed. 2020, 59, 5365.
  (l) Zhang, Q.; Xiong, Q.; Li, M.; Xiong, W.; Shi, B.; Lan, Y.; Lu, L.; Xiao, W. Angew. Chem. Int. Ed. 2020, DOI: 10.1002/anie.202005313
20. [20]
  Jiang, Y.; Yu, Z.; Zhang, Y.; Wang, B. Org. Lett. 2018, 20, 3728. doi: 10.1021/acs.orglett.8b01160
21. [21]
  (a) Dai, X.; Cheng, D.; Guan, B.; Mao, W.; Xu, X.; Li, X. J. Org. Chem. 2014, 79, 7212.
  (b) Dai, X.; Mao, R.; Guan, B.; Xu, X.; Li, X. RSC Adv. 2015, 5, 55290.
  (c) Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564.
  (d) Ye, Q.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2546.
  (e) Ye, H.; Ye, Q.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2046.
  (f) Ye, H.; Zhao, H.; Ren, S.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2019, 60, 1302.
22. [22]
  Becker, P.; Duhamel, T.; Stein, C. J.; Reiher, M.; Muñiz, K. Angew. Chem. Int. Ed. 2017, 56, 8004. doi: 10.1002/anie.201703611
23. [23]
  Uyanik, M.; Hayashi, H.; Ishihara, K. Science 2014, 345, 291. doi: 10.1126/science.1254976
24. [24]
  (a) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
  (b) Jiang, Y.; Chen, X.; Zheng, Y.; Xue, Z.; Shu, C.; Yuan, W.; Zhang, X. Angew. Chem. Int. Ed. 2011, 50, 7304.
25. [25]
  Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918. doi: 10.1021/ja047901i
26. [26]
  Ji, Y.; Trenkle, W. C.; Vowles, J. V. Org. Lett. 2006, 8, 1161. doi: 10.1021/ol053164z
27. [27]
  Jiang, J.; Wang, Y.; Zhang, X. ACS Catal. 2014, 4, 1570. doi: 10.1021/cs500261k
1. [1]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
2. [2]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
3. [3]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
4. [4]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
5. [5]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
6. [6]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
7. [7]
  Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012
8. [8]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
9. [9]
  Huiwei Ding , Bo Peng , Zhihao Wang , Qiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048
10. [10]
  Yushan Cai , Fang-Xing Xiao . Revisiting MXenes-based Photocatalysis Landscape: Progress, Challenges, and Future Perspectives. Acta Physico-Chimica Sinica, 2024, 40(8): 2306048-0. doi: 10.3866/PKU.WHXB202306048
11. [11]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-0. doi: 10.3866/PKU.WHXB202405016
12. [12]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
13. [13]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO₄/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212
14. [14]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
15. [15]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
16. [16]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
17. [17]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
18. [18]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
19. [19]
  Xinxin Wu . 基础有机化学教学中自由基重排反应的课程设计及其课程思政元素的融入. University Chemistry, 2025, 40(6): 316-325. doi: 10.12461/PKU.DXHX202408055
20. [20]
  Fangxuan Liu , Ziyan Liu , Guowei Zhou , Tingting Gao , Wenyu Liu , Bin Sun . 中空结构光催化剂. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-0. doi: 10.1016/j.actphy.2025.100071

Get Citation

PDF

XML

Metrics

PDF Downloads(124)
Abstract views(4248)
HTML views(564)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142