Citation: Zhang Jing, Chen Yiyun. Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions[J]. Acta Chimica Sinica, ;2017, 75(1): 41-48. doi: 10.6023/A16080416 shu

Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions

Zhang Jing ,
Chen Yiyun ^*,,

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Chen Yiyun, yiyunchen@sioc.ac.cn
Received Date: 15 August 2016

Fund Project: the National Basic Research Program of China 2014CB910304National Natural Science Foundation of China 21272260the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20020200National Natural Science Foundation of China 21472230

Figures(13)

The carboxyl and alkoxyl radicals generated from visible light photoredox reactions are important reaction intermediates in organic synthesis, which have witnessed conceivable progress recently. In this review, we focus on visible-light-induced photoredox methods to generate carboxyl radicals from carboxylate derivatives and carboxylates, as well as alkoxyl radicals from alcohol derivatives and alcohols, and briefly discuss their synthetic applications.
- visible light,
- radical reaction,
- carboxyl radical,
- alkoxyl radical
1. [1]
  Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632. doi: 10.1002/anie.201505731
3. [3]
  Huang, H.; Jia, K.; Chen, Y. ACS Catal. 2016, 6, 4983. doi: 10.1021/acscatal.6b01379
4. [4]
  Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564 (in Chinese). doi: 10.6023/cjoc201601012
5. [5]
  Čeković, Ž. Tetrahedron 2003, 59, 8073. doi: 10.1016/S0040-4020(03)01202-X
6. [6]
  Boto, A.; Hernandez, D.; Hernandez, R.; Suárez, E. J. Org. Chem. 2003, 68, 5310. doi: 10.1021/jo034442f
7. [7]
  Salamone, M.; Bietti, M. Acc. Chem. Res. 2015, 48, 2895. doi: 10.1021/acs.accounts.5b00348
8. [8]
  Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
9. [9]
  Schultz, D. M.; Yoon, T. P. Science2014, 343, 985.
10. [10]
  Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1039/B913880N
11. [11]
  Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828. doi: 10.1002/anie.201200223
12. [12]
  Hu, C. C.; Chen, Y. Y. Tetrahedron Lett. 2015, 56, 884. doi: 10.1016/j.tetlet.2014.12.034
13. [13]
  Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401. doi: 10.1021/ja00024a074
14. [14]
  Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576. doi: 10.1002/anie.v51.38
15. [15]
  Yang, J.; Zhang, J.; Qi, L.; Hu, C. C.; Chen, Y. Y. Chem. Commun. 2015, 51, 5275. doi: 10.1039/C4CC06344A
16. [16]
  Hu, C. C.; Chen, Y. Y. Org. Chem. Front. 2015, 2, 1352. doi: 10.1039/C5QO00187K
17. [17]
  Xie, J.; Xu, P.; Li, H. M.; Xue, Q. C.; Jin, H. M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2013, 49, 5672. doi: 10.1039/c3cc42672f
18. [18]
  He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451. doi: 10.1002/anie.201408522
19. [19]
  Kachkovskyi, G.; Faderl, C.; Reiser, O. Adv. Synth. Catal. 2013, 355, 2240. doi: 10.1002/adsc.201300221
20. [20]
  Zuo, Z. W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257. doi: 10.1021/ja501621q
21. [21]
  Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654. doi: 10.1021/jacs.5b02244
22. [22]
  Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R. P.; Qi, X. T.; Lan, Y.; Lei, A. W. Angew. Chem., Int. Ed. 2014, 53, 502. doi: 10.1002/anie.v53.2
23. [23]
  Chu, L. L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929. doi: 10.1002/anie.201501908
24. [24]
  Wang, G. Z.; Shang, R.; Cheng, W. M.; Fu, Y. Org. Lett. 2015, 17, 4830. doi: 10.1021/acs.orglett.5b02392
25. [25]
  Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196. doi: 10.1002/anie.201504559
26. [26]
  Le Vaillant, F.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200. doi: 10.1002/anie.201505111
27. [27]
  Wu, X. X.; Meng, C. N.; Yuan, X. Q.; Jia, X. T.; Qian, X. H.; Ye, J. X. Chem. Commun. 2015, 51, 11864. doi: 10.1039/C5CC04527D
28. [28]
  Luo, J.; Zhang, J. ACS Catal.2016, 6, 873. doi: 10.1021/acscatal.5b02204
29. [29]
  Huang, H. C.; Zhang, G. J.; Chen, Y. Y. Angew. Chem., Int. Ed. 2015, 54, 7872. doi: 10.1002/anie.201502369
30. [30]
  Tan, H.; Li, H. J.; Ji, W. Q.; Wang, L. Angew. Chem. Int. Ed. 2015, 54, 8374. doi: 10.1002/anie.201503479
31. [31]
  Zhang, J.; Li, Y.; Zhang, F. Y.; Hu, C. C.; Chen, Y. Y. Angew. Chem., Int. Ed. 2016, 55, 1872. doi: 10.1002/anie.201510014
32. [32]
  Wang, C. Y.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 13495. doi: 10.1002/anie.v55.43
33. [33]
  Jia, K. F.; Zhang, F. Y.; Huang, H. C.; Chen, Y. Y. J. Am. Chem. Soc. 2016, 138, 1514. doi: 10.1021/jacs.5b13066
34. [34]
  Yayla, H. G.; Wang, H. J.; Tarantino, K. T.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794. doi: 10.1021/jacs.6b06517
35. [35]
  Guo, J. J.; Hu, A. H.; Chen, Y. L.; Sun, J. F.; Tang, H. M.; Zuo, Z. W. Angew. Chem., Int. Ed. 2016, 55, 15319. doi: 10.1002/anie.v55.49
36. [36]
  Hu, X. Q.; Chen, J.; Chen, J. R.; Yan, D. M.; Xiao, W. J. Chem. Eur. J. 2016, 22, 14141. doi: 10.1002/chem.v22.40
1. [1]
  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
2. [2]
  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
3. [3]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
4. [4]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
5. [5]
  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
6. [6]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
7. [7]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
8. [8]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
9. [9]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
10. [10]
  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
11. [11]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
12. [12]
  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
13. [13]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
14. [14]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
15. [15]
  Honglian Liang , Xiaozhe Kuang , Fuping Wang , Yu Chen . Exploration and Practice of Integrating Ideological and Political Education into Physical Chemistry: a Case on Surface Tension and Gibbs Free Energy. University Chemistry, 2024, 39(10): 433-440. doi: 10.12461/PKU.DXHX202405073
16. [16]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
17. [17]
  Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034
18. [18]
  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-. doi: 10.3866/PKU.WHXB202405016
19. [19]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
20. [20]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046

Get Citation

PDF

XML

Metrics

PDF Downloads(156)
Abstract views(4147)
HTML views(1072)

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