Citation: Hu Yongke, Chen Lei, Li Bindong. Practical CuCl/DABCO/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant[J]. Chinese Chemical Letters, ;2018, 29(3): 464-466. doi: 10.1016/j.cclet.2017.10.036 shu

Practical CuCl/DABCO/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

Corresponding author: Li Bindong, libindong@njust.edu.cn

Received Date: 9 September 2017
Revised Date: 14 October 2017
Accepted Date: 27 October 2017
Available Online: 28 March 2017

Figures(3)

A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCl/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature. A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.
- Nitriles,
- Alcohols,
- Copper,
- 4-HO-TEMPO,
- Aerobic oxidation
1. [1]
  A. J. Fatiadi, Preparation and synthetic applications of cyano compounds, in: S. Patai, Z. Rappaport (Eds. ), Triple-Bonded Functional Groups, Wiley, New York, 1983, pp. 1057-1303.
2. [2]
  R.C. Larock, Comprenhensive Organic Transformations:A Guide to Functional Group Preparations, Wiley-VCH, New York, 1999.
3. [3]
  P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 40(2011) 5049-5067. doi: 10.1039/c1cs15004a
4. [4]
  W. Zhou, L. Zhang, N. Jiao, Angew. Chem. Int. Ed. 48(2009) 7094-7097. doi: 10.1002/anie.v48:38
5. [5]
  X.T. Ma, H. Xu, Y.L. Xiao, et al., Chin. Chem. Lett. 28(2017) 1336-1339. doi: 10.1016/j.cclet.2017.01.017
6. [6]
  D.S. Bhalerao, U.S. Mahajan, K.H. Chaudhari, K.G. Akamanchi, J. Org. Chem. 72(2007) 662-665. doi: 10.1021/jo0619074
7. [7]
  X. Zhang, J. Sun, Y. Ding, L. Yu, Org. Lett. 17(2015) 5840-5842. doi: 10.1021/acs.orglett.5b03011
8. [8]
  X.D. An, S. Yu, Org. Lett. 17(2015) 5064-5067. doi: 10.1021/acs.orglett.5b02547
9. [9]
  C.J. Fang, M.C. Li, X.Q. Hu, et al., Adv. Synth. Catal. 358(2016) 1157-1163. doi: 10.1002/adsc.201501130
10. [10]
  Q. Chen, C. Fang, Z. Shen, M. Li, Electrochem. Commun. 64(2016) 51-55. doi: 10.1016/j.elecom.2016.01.011
11. [11]
  X. Yang, Z. Fan, Z. Shen, M. Li, Electrochim. Acta 226(2017) 53-59. doi: 10.1016/j.electacta.2016.12.168
12. [12]
  Z. Fan, X. Yang, C. Chen, Z. Shen, M. Li, J. Electrochem. Soc.164(2017) G54-G58. doi: 10.1149/2.1561704jes
13. [13]
  J.M. Hoover, S.S. Stahl, J. Am. Chem. Soc. 133(2011) 16901-16910. doi: 10.1021/ja206230h
14. [14]
  Y. Hu, L. Chen, B. Li, Catal. Commun. 83(2016) 82-87. doi: 10.1016/j.catcom.2016.05.017
15. [15]
  Y. Hu, L. Chen, B. Li, Catal. Commun. 103(2018) 42-46. doi: 10.1016/j.catcom.2017.09.019
16. [16]
  S. Iida, H. Togo, Tetrahedron 63(2007) 8274-8281. doi: 10.1016/j.tet.2007.05.106
17. [17]
  K.R. Reddy, C.U. Maheswari, M. Venkateshwar, S. Prashanthi, M.L. Kantam, Tetrahedron Lett. 50(2009) 2050-2053. doi: 10.1016/j.tetlet.2009.02.057
18. [18]
  B.V. Rokade, S.K. Malekar, K.R. Prabhu, Chem. Commun. 48(2012) 5506-5508. doi: 10.1039/c2cc31256e
19. [19]
  S. Yamazaki, Y. Yamazaki, Chem. Lett. 19(1990) 571-574. doi: 10.1246/cl.1990.571
20. [20]
  G.D. McAllister, C.D. Wilfred, R.J.K. Taylor, Synlett (2002) 1291-1292.
21. [21]
  T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 105(2005) 2329-2363. doi: 10.1021/cr050523v
22. [22]
  T. Oishi, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 48(2009) 6286-6288. doi: 10.1002/anie.200900418
23. [23]
  T. Ishida, H. Watanabe, T. Takei, et al., Appl. Catal. A:Gen. 425-426(2012) 85-90.
24. [24]
  R.V. Jagadeesh, H. Junge, M. Beller, Nat. Commun. 5(2014) 4123.
25. [25]
  S.S. Shang, L.Y. Wang, W. Dai, et al., Catal. Sci. Technol. 6(2016) 5746-5753. doi: 10.1039/C6CY00195E
26. [26]
  S. Shang, W. Dai, L. Wang, Y. Lv, S. Gao, Chem. Commun. 53(2017) 1048-1051. doi: 10.1039/C6CC09151B
27. [27]
  B.L. Ryland, S.S. Stahl, Angew. Chem. Int. Ed. 53(2014) 8824-8838. doi: 10.1002/anie.201403110
28. [28]
  W. Yin, C. Wang, Y. Huang, Org. Lett. 15(2013) 1850-1853. doi: 10.1021/ol400459y
29. [29]
  C. Tao, F. Liu, Y. Zhu, W. Liu, Z. Cao, Org. Biomol. Chem. 11(2013) 3349-3354. doi: 10.1039/c3ob00002h
30. [30]
  L.M. Dornan, Q. Cao, J.C. Flanagan, et al., Chem. Commun. 49(2013) 6030-6032. doi: 10.1039/c3cc42231c
31. [31]
  S.U. Dighe, D. Chowdhury, S. Batra, Adv. Synth. Catal. 356(2014) 3892-3896. doi: 10.1002/adsc.v356.18
32. [32]
  E. Fritz-Langhals, Org. Process Res. Dev. 9(2005) 577-582. doi: 10.1021/op050040t
33. [33]
  X. Wang, X. Liang, Chin. J. Catal. 29(2008) 935-939. doi: 10.1016/S1872-2067(08)60075-3
34. [34]
  J.M. Hoover, B.L. Ryland, S.S. Stahl, J. Am. Chem. Soc. 135(2013) 2357-2367. doi: 10.1021/ja3117203
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