Citation: Yang Jun, Fu Ting, Long Yang, Zhou Xiangge. Progress in Catalytic C-H Activation Reactions in Water[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1111-1116. doi: 10.6023/cjoc201702045 shu

Progress in Catalytic C-H Activation Reactions in Water

College of Chemistry, Sichuan University, Chengdu 610064

Corresponding author: Zhou Xiangge, zhouxiangge@scu.edu.cn
Received Date: 27 February 2017
Revised Date: 22 March 2017

Fund Project: the National Natural Science Foundation of China J1310008the National Natural Science Foundation of China Nos. 21472128

Figures(4)

C-H bond functionalization is one of the hot spots in the research field of organic chemistry, and selective C-H activation is a challenging project. Among these reactions, organic solvent is normally used as reaction media. Using cheap, environmentally friendly water as reaction solvent would be in line with the requirements of "green chemistry" and low-carbon sustainable development. This paper reviews the recent progress of aqueous catalyzed C-H functionalization reactions, including hybridized sp-, sp²-, and sp³-C-H bonds.
- catalysis,
- C-H activation,
- water,
- green chemistry
1. [1]
  Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283 (in Chinese).
2. [2]
  Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
3. [3]
  Hull, K.; Sanford, M. J. Am. Chem. Soc. 2007, 129, 11904.
4. [4]
  Desai, L.; Stowers, K.; Sanford, M. J. Am. Chem. Soc. 2008, 130, 13285.
5. [5]
  Joo, J.; Guo, P.; Sames, D. J. Org. Chem. 2013, 78, 738.
6. [6]
  Tan, J.; Chen, Y.; Li, H.; Yasuda, N. J. Org. Chem. 2014, 79, 8871.
7. [7]
  Batchu, H.; Bhattacharyya, S.; Kant, R.; Batra, S. J. Org. Chem. 2015, 80, 7360.
8. [8]
  Brahim, M.; Smari, I.; Ammar, H.; Hassine, B.; Soulé, J.; Doucet, H. Org. Chem. Front. 2015, 2, 917.
9. [9]
  Testa, C.; Roger, J.; Scheib, S.; Fleurat-Lessard, P.; Hierso, J. Adv. Synth. Catal. 2015, 357, 2913.
10. [10]
  Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094.
11. [11]
  Kim, M.; Kwak, J.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 8935.
12. [12]
  Gong, T.; Xiao, B.; Cheng, W.; Su, W.; Xu, J.; Liu, Z.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 10630.
13. [13]
  Reddy, V.; Qiu, R.; Iwasaki, T.; Kambe, N. Org. Lett. 2013, 15, 1290.
14. [14]
  Wang, H.; Schrçder, N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386.
15. [15]
  Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780.
16. [16]
  Zhang, P.; Hong, L.; Li, G.; Wang, R. Adv. Synth. Catal. 2015, 357, 345.
17. [17]
  Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
18. [18]
  Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619.
19. [19]
  Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y. Chem. Lett. 2008, 37, 994.
20. [20]
  Kumar, P.; Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145.
21. [21]
  Ackermann, L.; Vicente, R.; Potukuchi, H.; Pirovano, V. Org. Lett. 2010, 12, 5032.
22. [22]
  Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Green Chem. 2011, 13, 3075.
23. [23]
  Muralirajan, K.; Parthasarathy, K.; Cheng, C. Org. Lett. 2012, 14, 4262.
24. [24]
  Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. J. Org. Chem. 2013, 78, 638.
25. [25]
  Schinkel, M.; Marek, I.; Ackermann, L. Angew. Chem., Int. Ed. 2013, 52, 3977.
26. [26]
  Gonell, S.; Peris, E. ACS Catal. 2014, 4, 2811.
27. [27]
  Wei, C.; Li, C. J. Am. Chem. Soc. 2002, 124, 5638.
28. [28]
  Wei, C.; Li, C. J. Am. Chem. Soc. 2003, 125, 9584.
29. [29]
  Yao, X.; Li, C. Org. Lett. 2005, 7, 4395.
30. [30]
  Yao, X.; Li, C. Org. Lett. 2006, 8, 1953.
31. [31]
  Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Angew. Chem., Int. Ed. 2010, 49, 6629.
32. [32]
  Ackermann, L.; Lygin, A. Org. Lett. 2012, 14, 764.
33. [33]
  Ackermann, L.; Pospech, J.; Potukuchi, H. Org. Lett. 2012, 14, 2146.
34. [34]
  Wu, Z. Luo, F.; Chen, S.; Li, Z.; Xiang, H.; Zhou, X. Chem. Commun. 2013, 49, 7653.
35. [35]
  Wu, Z.; Chen, S.; Hu, C.; Li, Z.; Xiang, H.; Zhou, X. ChemCatChem 2013, 5, 2839.
36. [36]
  Lu, M.; Lu, P.; Xu, Y.; Loh, T. Org. Lett. 2014, 16, 2614.
37. [37]
  Luo, F.; Yang, J.; Li, Z.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2015, 2463.
38. [38]
  Sun, S.; Shang, M.; Wang, H.; Lin, H.; Dai, H.; Yu, J. J. Org. Chem. 2015, 80, 8843.
39. [39]
  Gong, H.; Zeng, H.; Zhou, F.; Li, C. Angew. Chem., Int. Ed. 2015, 54, 5718.
40. [40]
  Xiao, F.; Chen, S.; Huang, H. Deng, G. Eur. J. Org. Chem. 2015, 7919.
41. [41]
  Ohnmacht, S.; Mamone, P.; Culshaw, A. Greaney, M. Chem. Commun. 2008, 1241.
42. [42]
  Ohnmacht, S.; Culshaw, A.; Greaney, M. Org. Lett. 2010, 12, 224.
43. [43]
  Ramirez, N.; Bosque, I.; Gonzalez-Gomez, J. Org. Lett. 2015, 17, 4550.
44. [44]
  Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144.
45. [45]
  Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G. Green Chem. 2016, 18, 1538.
46. [46]
  Arumugam, V.; Kaminsky, W.; Nallasamy, D. Green Chem. 2016, 18, 3295.
47. [47]
  Hu, J.; Lan, T.; Sun, Y.; Chen, H.; Yao, J.; Rao, Y. Chem. Commun. 2015, 51, 14929.
48. [48]
  Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805 (in Chinese).
49. [49]
  Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org. Chem. 2008, 73, 7365.
50. [50]
  Yi, C.; Kwon, K.; Lee, D. Org. Lett. 2009, 11, 1567.
51. [51]
  Pierce, C.; Hilinski, M. Org. Lett. 2014, 16, 6504.
1. [1]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
2. [2]
  Xiaoyu Wang , Yifan Li , Ruibo Liu , Li An , Dan Qu , Yichang Liu , Zaicheng Sun . Graphitic Carbon Nitride Catalyzed Photochemical Minisci Reaction: A Comprehensive Experimental Design Derived from Scientific Research. University Chemistry, 2026, 41(4): 363-371. doi: 10.12461/PKU.DXHX202502065
3. [3]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
4. [4]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . Electrochemical CO₂ Reduction to C₂₊ Products with Ampere-Level Current on Carbon-Modified Copper Catalysts. Acta Physico-Chimica Sinica, 2025, 41(3): 100024-0. doi: 10.3866/PKU.WHXB202404012
5. [5]
  Yongxin LIU , Xingchen LI , Hongjia LIU , Danni LI , Tao ZHANG , Xi CHEN . Enhancement effect of Fe₃O₄ conversion to MIL-100(Fe) on activation of persulfate for degradation of antibiotic. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2503-2513. doi: 10.11862/CJIC.20250169
6. [6]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
7. [7]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
8. [8]
  Xiaomin Kang , Chuanbao Jiao . Application of Metal-Organic Frameworks in CO₂ Catalytic Conversion: Promoting “Double Carbon” Actions for a Beautiful China. University Chemistry, 2026, 41(2): 208-217. doi: 10.12461/PKU.DXHX202503011
9. [9]
  Tianhao GE , Sirong LU , Zhiyin XIAO , Wei ZHONG . Synthesis of porphyrin-based ionic polymeric materials for catalytic application in CO₂ conversion. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 722-736. doi: 10.11862/CJIC.20250312
10. [10]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
11. [11]
  Qingtao CHEN , Xiangdong SHI , Xianghai RAO , Liying JIANG , Chunxiao JIA , Fenghua CHEN . Catalytic and in situ surface-enhanced Raman scattering detection properties of graphene oxide/gold nanorod assembly. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 120-128. doi: 10.11862/CJIC.20250091
12. [12]
  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
13. [13]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
16. [16]
  Yifan Liu , Haonan Peng . AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry. University Chemistry, 2025, 40(7): 189-199. doi: 10.12461/PKU.DXHX202405182
17. [17]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
18. [18]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
19. [19]
  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
20. [20]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

Get Citation

PDF

XML

Metrics

PDF Downloads(27)
Abstract views(2843)
HTML views(419)

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