Citation: Zheng Dagui, Zhou Anxi, Zhu Xianhong, Zheng Hongfu, Sun Xiangqian. An Efficient Dimethylacetamide-Promoted Conversion ofAlcohols to Alkyl Chlorides[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 137-142. doi: 10.6023/cjoc201507020 shu

An Efficient Dimethylacetamide-Promoted Conversion ofAlcohols to Alkyl Chlorides

1.
Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, Shangrao Normal University, Shangrao 334001

Corresponding author: Zheng Dagui, daguizheng@163.com
Received Date: 20 July 2015
Revised Date: 15 September 2015

Fund Project: the Xinjiang 866 Project of Excellence Talent 2013-37

Figures(1)

A simple and efficient method for the conversion of alcohols to the corresponding alkyl chlorides by using dimethylacetamide (DMAc) as a promoter was developed. It provides a new and practical protocol for the synthesis of alkyl chlorides.
- dimethylacetamide,
- alcohol,
- alkyl chlorides,
- synthesis
1. [1]
  Sun, L. L.; Peng, G. S.; Niu, H. M.; Wang, Q.; Li, C. B. Synthesis 2008, 3919.
2. [2]
  Denton, R. M.; An, J.; Adeniran, B. Chem. Commun. 2010, 46, 3025. doi: 10.1039/c002825h
3. [3]
  Denton, R. M.; An, J.; Adeniran, B.; Blake, A. J.; Lewis, W.; Poulton, A. M. J. Org. Chem. 2011, 76, 6749. doi: 10.1021/jo201085r
4. [4]
  Kimura, Y.; Matsuura, D. Int. J. Org. Chem. 2013, 3, 1.
  (b) Kimura, Y.; Matsuura, D. Hanawa, T.; Kobayashi, Y. Tetrahedron Lett. 2012, 53, 1116.
5. [5]
  Dubey, A.; Upadhyay, A. K.; Kumar, P. Tetrahedron Lett. 2010, 51, 744. doi: 10.1016/j.tetlet.2009.11.131
6. [6]
  Luca, L. D.; Giacomelli, G.; Porcheddu, A. Org. Lett, 2002, 4, 553. doi: 10.1021/ol017168p
7. [7]
  Roy, S.; Das, T.; Saha, M.; Chaudhuri, S. K.; Bhar, S. Synth. Commun. 2007, 37, 4367. doi: 10.1080/00397910701578206
8. [8]
  Cadis, E.; Gheorghe, A. V.; Fey, L. Rev. Chim. (Bucharest) 1987, 38, 264.
  (b) Qian, X. Q.; Zhou, H.; Zhan, X. P.; Liu, Z. L.; Mao, Z. M. Chin. J. Org. Chem. 2012, 32, 2223 (in Chinese).
  (钱晓庆, 周恒, 詹晓平, 刘增路, 毛振民, 有机化学, 2012, 32, 2223.)
9. [9]
  Vanos, C. M.; Lambert, T. H. Angew Chem., Int. Ed. 2011, 50, 12222. doi: 10.1002/anie.v50.51
10. [10]
  Kelly, B. D.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 13930. doi: 10.1021/ja906520p
11. [11]
  Nguyen, T. V.; Bekensir, A. Org. Lett. 2014, 16, 1720. doi: 10.1021/ol5003972
12. [12]
  Chaudhari, S. S.; Akamanchi, K. G. Synlett 1999, 1763.
13. [13]
  Ayala, C. E.; Villalpando, A.; Nguyen, A. L.; McCandless, G. T.; Kartika, R. Org. Lett. 2012, 14, 3676. doi: 10.1021/ol301520d
14. [14]
  Thirumamagal, B. T. S.; Narayanasamy, S.; Venkatesan, R. Synth. Commun. 2008, 38, 2820. doi: 10.1080/00397910801979338
15. [15]
  Hu, Y. L.; Lu, M.; Ge, Q.; Wang, P. C.; Zhang, S. B.; Lu, T. T. J. Chil. Chem. Soc. 2010, 55, 97.
16. [16]
  Sun, Y. Y.; Yi, J.; Lu, X.; Zhang, Z. Q.; Xiao, B.; Fu, Y. Chem. Commun. 2014, 50, 11060. doi: 10.1039/C4CC05376A
17. [17]
  Ramin, G. V., ; Lotfi, S.; Arash, G. C. Bull. Korean Chem. Soc. 2013, 34, 820. doi: 10.5012/bkcs.2013.34.3.820
18. [18]
  Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 4258. doi: 10.1021/ja210361z
19. [19]
  Goerner, G. L.; Nametz, R. C. J. Am. Chem. Soc. 1951, 73, 2940.
20. [20]
  Yasuda, M.; Yamasaki, S.; Onishi, Y.; Baba, A. J. Am. Chem. Soc. 2004, 126, 7186. doi: 10.1021/ja048688t
21. [21]
  Feng, X.; Sun, A.; Zhang, S.; Yu, X.; Bao, M. Org. Lett. 2013, 15, 108. doi: 10.1021/ol303135e
22. [22]
  Richter, R.; Tucker, B. J. Org. Chem. 1983, 48, 2625. doi: 10.1021/jo00163a047
23. [23]
  Onishi, Y.; Ogawa, D.; Yasuda, M.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13690. doi: 10.1021/ja0283246
24. [24]
  Liu, Y.; Xu, Y.; S. Jung, H.; Chae, J. Synlett 2012, 2692.
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沈阳化工大学材料科学与工程学院沈阳 110142