Citation: Fu Wenqiang, Tan Ping, Deng Wei, Xiang Jiannan. Efficient Hydrolysis of Haloalkynes to α-Haloketones in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1501-1505. doi: 10.6023/cjoc201610031 shu

Efficient Hydrolysis of Haloalkynes to α-Haloketones in Ionic Liquid

Fu Wenqiang ^a ,
Tan Ping ^b ,
Deng Wei ^a ,
Xiang Jiannan ^a,*,,

a.
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
b.
Hunan Mechanical and Electrical Polytechnic, Changsha 410151

Corresponding author: Xiang Jiannan, jnxiang@hnu.edu.cn
Received Date: 18 October 2016
Revised Date: 30 December 2016

Fund Project: the Planned Science and Technology Project of Hunan Province 2015WK3003the Scientific Research Fund of Hunan Provincial Education Department 14C0405

Figures(1)

The haloalkynes were hydrolyzed to α-haloketones by sulfuric acid promotion in ionic liquids (ILs) with 85%~94% yields. The ILs-H₂SO₄ reaction system could be easily recycled (more five times) without any effect for reaction yield. At the same time, a wide scope of substrates haloalkynes were proper in this reaction system and a series of α-chloro/bromo/iodo acetophenones with different substituent (such as methyl, methoxyl, hydroxyl, nitro etc.) and aliphatic α-haloketones have been obtained in good yields.
- ionic liquid,
- haloalkynes,
- hydration,
- α-haloketones,
- recyclable
1. [1]
  (a) Erian, A. W.; Sherif, S. M.; Gaber, H. M. Molecules 2003, 8, 793.
  (b) Zhang, H.; Wei, Q.; Wei, S.; Qu, J.; Wang, B. Eur. J. Org. Chem. 2016, 3373.
2. [2]
  De Kimpe, N.; Verhé, R. The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, Ed.: Patai, S., Wiley, Chichester, UK, 1988, pp. 1~119.
3. [3]
  (a) Ostrowski, T.; Golankiewicz, B.; De Clercq, E.; Andrei, G.; Snoeck, R. Eur. J. Med. Chem. 2009, 44, 3313.
  (b) Conde, S.; Pérez, D. I.; Martínez, A.; Perez, C.; Moreno, F. J. J. Med. Chem. 2003, 46, 4631.
4. [4]
  (a) Morton, H. E.; Leanna, M. R. Tetrahedron Lett. 1993, 34, 4481.
  (b) Patil, R. D.; Joshi, G.; Adimurthy, S.; Ranu, B. C. Tetrahedron Lett. 2009, 50, 2529.
  (c) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Chem. Commun. 2004, 470.
  (d) Meshram, H. M.; Reddy, P. N.; Vishnu, P.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 991.
  (e) Pravst, I.; Zupan, M.; Stavber, S. Tetrahedron 2008, 64, 5191.
  (f) Kosower, E. M.; Wu, G. S. J. Org. Chem. 1963, 28, 633.
  (g) Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Fujisaki, S.; Maeno, K.; Okamoto, T. Synthesis 1988, 545.
  (h) Dieter, R. K.; Nice, L. E.; Velu, S. E. Tetrahedron Lett. 1996, 37, 2377.
5. [5]
  Xie, L.; Wu, Y.; Yi, W.; Zhu, L.; Xiang, J.; He, W. J. Org. Chem. 2013, 78, 9190. doi: 10.1021/jo401437w
6. [6]
  Zou, H.; He, W.; Dong, Q.; Wang, R.; Yi, N.; Jiang, J.; Peng, D.; He, W. Eur. J. Org.Chem. 2016, 116.
7. [7]
  (a) Chen, Z.; Ye, D.; Ye, M.; Zhou, Z.; Li, S.; Liu, L. Tetrahedron Lett. 2014, 55, 1373.
  (b) Zeng, M.; Huang, R.; Li, W.; Liu, X.; He, F.; Zhang, Y.; Xiao, F. Tetrahedron Lett. 2016, 72, 3818.
8. [8]
  (a) Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Appl. Catal. A: Gen. 2010, 373, 1.
  (b) Hu, Y.; Guo, Z.; Lue, B. M.; Xu, X. J. Agric. Food Chem. 2009, 57, 3845.
  (c) Tzani, A.; Douka, A.; Papadopoulos, A.; Pavlatou, E. A.; Voutsas, E.; Detsi, A. ACS Sustainable Chem. Eng. 2013, 1, 1180.
9. [9]
  Wong, W.; Ho, K.; Lee, L.; Lam, K.; Zhou, Z.; Chan, T.; Wong, K. ACS Catal. 2011, 1, 116. doi: 10.1021/cs100016h
10. [10]
  Wei, Q. L.; Zhang, S. S.; Gao, J.; Li, W. H.; Xu, L. Z.; Yu, Z. G. Bioorg. Med. Chem. 2006, 14, 7146. doi: 10.1016/j.bmc.2006.06.065
11. [11]
  Reddy Bodireddy, M.; Gangi, R. N. C. Synth. Commun. 2013, 43, 2603. doi: 10.1080/00397911.2012.725264
12. [12]
  Guan, X.; AlMisbaa, Z.; Huang, K. Arabian J. Chem. 2015, 8, 892. doi: 10.1016/j.arabjc.2014.01.024
13. [13]
  Sugiura, A.; Kepner, R. E.; Webb, A. D. J. Org. Chem. 1962, 27, 773. doi: 10.1021/jo01050a020
14. [14]
  Jiang, Q.; Sheng, W.; Guo, C. Green Chem. 2013, 15, 2175 doi: 10.1039/c3gc40515j
15. [15]
  Rosenmund, K. W. Chem. Ber. 1957, 90, 1922. doi: 10.1002/(ISSN)1099-0682
16. [16]
  Lapointe, D.; Markiewicz, T.; Whipp, C. J.; Toderian, A.; Fagnou, K. J. Org. Chem. 2011, 76, 749. doi: 10.1021/jo102081a
17. [17]
  Judefind, W. L. J. Am. Chem. Soc. 1920, 42, 1043. doi: 10.1021/ja01450a019
18. [18]
  Arrieta, A. Synth. Commun. 1984, 14, 939. doi: 10.1080/00397918408063764
19. [19]
  Suzuki, M. Yakugaku Zasshi 1952, 72, 305. doi: 10.1248/yakushi1947.72.3_305
20. [20]
  Antunes, H.; Fardelone, L. C.; Rodrigues, J. A. R.; Moran, P. J. S. Tetrahedron: Asymmetry 2004, 15, 2615. doi: 10.1016/j.tetasy.2004.07.029
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