Citation: Liu Lantao, Chen Yingyinga, Zhang An'an, Liu Xue, Zhang Li, Bai Jingru, Li Heng, Mao Guoliang. Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 475-481. doi: 10.6023/cjoc201808013 shu

Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones

Liu Lantao ^a,, ,
Chen Yingyinga ^a,b ,
Zhang An'an ^a ,
Liu Xue ^a,c ,
Zhang Li ^a ,
Bai Jingru ^a ,
Li Heng ^c ,
Mao Guoliang ^b,,

a.
College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000
b.
College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318
c.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Liu Lantao, liult05@iccas.ac.cn Mao Guoliang, maoguoliang@nepu.edu.cn
Received Date: 13 August 2018
Revised Date: 3 September 2018
Available Online: 10 February 2018
Fund Project: the National Natural Science Foundation of China 21572126the Program for Science & Technology Innovation Talents in Universities of Henan Province 14HASTIT016the Program of Science and Technology Innovation Talents of Henan Province 2018JQ0011Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011)

Figures(2)

Allylic amines moiety exists extensively in natural products, medicines and functional materials. In addition, they are also a kind of versatile building blocks for organic synthesis. Using CH₃CN as solvent, the palladium catalyzed allyl amination of cinnamyl carbonate and acylhydrazone compounds was realized under argon. The linear product was formed selectively and the up to 99% yield was obtained. The reaction has features of base free, mild reaction condition, simple operation and broad substrate scope.
- paladium catalysis,
- allylic amination,
- cinnamyl carbonate
1. [1]
2. [2]
3. [3]
  (a) Monk, J. P.; Brogden, R. N. Drugs 1991, 42, 659.
  (b) Birnbaum, J. E. J. Am. Acad. Dermatol. 1990, 23, 782.
  (c) Xu, Z.; Wang, D. S.; Yu, X.; Yang Y.; Wang, D. Adv. Synth. Catal. 2017, 359, 3332.
4. [4]
  (a) Stuetz, A.; Petranyi, G. J. Med. Chem. 1984, 27, 1539.
  (b) Rudisill, D. E.; Castonguay, L. A.; Me, J. K. Tetrahedron Lett. 1988, 29, 1509.
  (c) Balfour, J. A.; Fauids, D. Drugs 1992, 43, 259.
  (d) Ge, C.; Sang, X.; Yao, W.; Zhang L.; Wang, D. Green Chem. 2018, 20, 1805.
5. [5]
  (a) Andersson, P. G.; Backvall, J. E. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1859.
  (b) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
  (c) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, Vol. 2, p. 699.
  (d) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1051.
6. [6]
  (a) Ranerand, K. D.; Ward, A. D. Aust. J. Chem. 1991, 44, 1749.
  (b) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
  (c) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469.
7. [7]
  (a) Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1028.
  (b) Caddick, S.; Koe, W. Tetrahedron Lett. 2002, 43, 9347.
  (c) Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.
  (d) Lu, T.; Lu, Z.; Ma, Z. X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.
8. [8]
  Cho, C. S.; Kim, J. S.; Oh, B. H. Tetrahedron 2000, 56, 7747. doi: 10.1016/S0040-4020(00)00694-3
9. [9]
  Cui, X. M. Chlor-Alkali Ind. 2000, 5, 172192(in Chinese).
10. [10]
11. [11]
  Lee, O. Y.; Law, K. L.; Yang, D. Org. Lett. 2009, 11, 3302. doi: 10.1021/ol901111g
12. [12]
  (a) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
  (b) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
  (c) Zhou, C. Y.; Zhu, S. F.; Wang, L. X., Zhou, Q. L. J. Am. Chem. Soc. 2010, 132, 10955.
  (d) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026.
13. [13]
  (a) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C. G.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (b) Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314.
14. [14]
  (a) Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E.; Hoegberg, T.; Ulff, B. J. Org. Chem. 1981, 46, 3479.
  (b) You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471.
  (c) Nagano, T.; Kobayashi, S. J. Am. Chem. Soc. 2009, 131, 4200.
  (d) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (e) Dubovyk, I.; Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2013, 78, 1559.
  (f) Cai, A. J.; Guo, W. S.; Martínez-Rodríguez, L.; Kleij, A. W. J. Am. Chem. Soc. 2016, 138, 14194.
  (g) Li, Y. G.; Li, L.; Yang, M. Y.; Kantchev, E. A. B. J. Org. Chem. 2017, 82, 4907.
15. [15]
  (a) Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427.
  (b) Evans, P.; Grange, R.; Clizbe, E. Synthesis 2016, 48, 2911.
  (c) Guo, W.; Cai, A.; Xie, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2017, 56, 11797.
  (d) Xia, C.; Shen, J.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 4251.
  (e) Wang, Y. N.; Wang, B. C.; Zhang, M. M.; Gao, X. W.; Li, T. R.; Lu, L. Q.; Xiao, W. J. Org. Lett. 2017, 19, 4094.
16. [16]
  Yao, L.; Wang, C. J. Adv. Synth. Catal. 2015, 357, 384. doi: 10.1002/adsc.201400790
17. [17]
  Lu, B.; Feng, B.; Ye, H.; Chen, J. R.; Xiao, W. J. Org. Lett. 2018, 20, 3473. doi: 10.1021/acs.orglett.8b01226
18. [18]
  Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13(in Chinese).
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