Reviews

Progress in Catalytic C-H Activation Reactions in Water

  • Yang Jun ,
  • Fu Ting ,
  • Long Yang ,
  • Zhou Xiangge
Expand
  • College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2017-02-27

  Revised date: 2017-03-22

  Online published: 2017-03-31

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21472128, J1310008).

Abstract

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.

Cite this article

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

References

[1] Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283 (in Chinese). (廖港, 史炳锋, 化学学报, 2015, 73, 1283.)
[2] Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese). (张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
[3] Hull, K.; Sanford, M. J. Am. Chem. Soc. 2007, 129, 11904.
[4] Desai, L.; Stowers, K.; Sanford, M. J. Am. Chem. Soc. 2008, 130, 13285.
[5] Joo, J.; Guo, P.; Sames, D. J. Org. Chem. 2013, 78, 738.
[6] Tan, J.; Chen, Y.; Li, H.; Yasuda, N. J. Org. Chem. 2014, 79, 8871.
[7] Batchu, H.; Bhattacharyya, S.; Kant, R.; Batra, S. J. Org. Chem. 2015, 80, 7360.
[8] Brahim, M.; Smari, I.; Ammar, H.; Hassine, B.; Soulé, J.; Doucet, H. Org. Chem. Front. 2015, 2, 917.
[9] Testa, C.; Roger, J.; Scheib, S.; Fleurat-Lessard, P.; Hierso, J. Adv. Synth. Catal. 2015, 357, 2913.
[10] Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094.
[11] Kim, M.; Kwak, J.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 8935.
[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] Reddy, V.; Qiu, R.; Iwasaki, T.; Kambe, N. Org. Lett. 2013, 15, 1290.
[14] Wang, H.; Schrçder, N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386.
[15] Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780.
[16] Zhang, P.; Hong, L.; Li, G.; Wang, R. Adv. Synth. Catal. 2015, 357, 345.
[17] Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
[18] Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619.
[19] Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y. Chem. Lett. 2008, 37, 994.
[20] Kumar, P.; Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145.
[21] Ackermann, L.; Vicente, R.; Potukuchi, H.; Pirovano, V. Org. Lett. 2010, 12, 5032.
[22] Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Green Chem. 2011, 13, 3075.
[23] Muralirajan, K.; Parthasarathy, K.; Cheng, C. Org. Lett. 2012, 14, 4262.
[24] Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. J. Org. Chem. 2013, 78, 638.
[25] Schinkel, M.; Marek, I.; Ackermann, L. Angew. Chem., Int. Ed. 2013, 52, 3977.
[26] Gonell, S.; Peris, E. ACS Catal. 2014, 4, 2811.
[27] Wei, C.; Li, C. J. Am. Chem. Soc. 2002, 124, 5638.
[28] Wei, C.; Li, C. J. Am. Chem. Soc. 2003, 125, 9584.
[29] Yao, X.; Li, C. Org. Lett. 2005, 7, 4395.
[30] Yao, X.; Li, C. Org. Lett. 2006, 8, 1953.
[31] Arockiam, P.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. Angew. Chem., Int. Ed. 2010, 49, 6629.
[32] Ackermann, L.; Lygin, A. Org. Lett. 2012, 14, 764.
[33] Ackermann, L.; Pospech, J.; Potukuchi, H. Org. Lett. 2012, 14, 2146.
[34] Wu, Z. Luo, F.; Chen, S.; Li, Z.; Xiang, H.; Zhou, X. Chem. Commun. 2013, 49, 7653.
[35] Wu, Z.; Chen, S.; Hu, C.; Li, Z.; Xiang, H.; Zhou, X. ChemCatChem 2013, 5, 2839.
[36] Lu, M.; Lu, P.; Xu, Y.; Loh, T. Org. Lett. 2014, 16, 2614.
[37] Luo, F.; Yang, J.; Li, Z.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2015, 2463.
[38] Sun, S.; Shang, M.; Wang, H.; Lin, H.; Dai, H.; Yu, J. J. Org. Chem. 2015, 80, 8843.
[39] Gong, H.; Zeng, H.; Zhou, F.; Li, C. Angew. Chem., Int. Ed. 2015, 54, 5718.
[40] Xiao, F.; Chen, S.; Huang, H. Deng, G. Eur. J. Org. Chem. 2015, 7919.
[41] Ohnmacht, S.; Mamone, P.; Culshaw, A. Greaney, M. Chem. Commun. 2008, 1241.
[42] Ohnmacht, S.; Culshaw, A.; Greaney, M. Org. Lett. 2010, 12, 224.
[43] Ramirez, N.; Bosque, I.; Gonzalez-Gomez, J. Org. Lett. 2015, 17, 4550.
[44] Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144.
[45] Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G. Green Chem. 2016, 18, 1538.
[46] Arumugam, V.; Kaminsky, W.; Nallasamy, D. Green Chem. 2016, 18, 3295.
[47] Hu, J.; Lan, T.; Sun, Y.; Chen, H.; Yao, J.; Rao, Y. Chem. Commun. 2015, 51, 14929.
[48] Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805 (in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
[49] Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org. Chem. 2008, 73, 7365.
[50] Yi, C.; Kwon, K.; Lee, D. Org. Lett. 2009, 11, 1567.
[51] Pierce, C.; Hilinski, M. Org. Lett. 2014, 16, 6504.

Outlines

/