Citation: Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1205-1212. doi: 10.6023/cjoc201701051 shu

Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes

Xu Dingjian ^a ,
Meng Lichen ^a ,
Xu Hang ^a ,
Yao Xiaoquan ^a,*,,

a.
Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016

Corresponding author: Yao Xiaoquan, yaoxq@nuaa.edu.cn
Received Date: 27 January 2017
Revised Date: 21 March 2017

Fund Project: by the National Natural Science Foundation of China 21172107by the National Natural Science Foundation of China 21472092

Figures(1)

A copper iodide catalyzed reaction of aldehydes and t-butyl hydroperoxide (TBHP) was developed for the synthesis of peresters in the presence of bipyridine ligand under mild and neat conditions. The addition of bipyridine ligand increased the catalytic activities of copper catalyst significantly and triggered the reaction. The reaction showed good tolerance to various substrates, and good to excellent yields were obtained. Furthermore, a one-pot synthesis of allylic esters was also achieved by the addition of cyclohexene to the reaction mixture under neat condition at relative lower temperature.
- copper catalyzed,
- N-donor ligand,
- C-H activation,
- perester,
- allylic ester,
- one-pot synthesis,
- neat
1. [1]
2. [2]
  Some recent examples: (a) Sarkar, S.; Laha, R. M.; Mitra, R. N.; Maiti D. K. ACS Omega 2016, 1, 981. (b) Tang, S.; Zeng, L.; Liu, Y.; Lei, A. Angew. Chem., Int. Ed. 2015, 54, 15850. (c) Zhou, B.; Du, J.; Yang, Y.; Li, Y. Org. Lett. 2013, 15, 2934. (d) Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 332.
3. [3]
  Some examples: (a) Mo, J.; Wang, L.; Cui, X. Org. Lett. 2015, 17, 4960. (b) Spantulescu, M. D.; Boudreau, M. A.; Vederas, J. C. Org. Lett. 2009, 11, 645. (c) Yamago, S. J. Polym. Sci: Polym. Chem. Ed. 2006, 44, 1. (d) Wang, L.; Liu, X.; Li, Y. Langmuir 1998, 14, 6879. (e) Sosnovsky, G.; Zaret, E. H.; Konieczny, M. J. Org. Chem. 1972, 37, 2267 and the references therein.
4. [4]
  Lu, M. Y.; Bao, R.; Liu, W.; Li, Y. J. Org. Chem. 1995, 60, 5341. doi: 10.1021/jo00121a068
5. [5]
  Bolje, A.; Hohloch, S.; Urankar, D.; Pevec, A.; Gazvoda, M.; Sarkar, B.; Košmrlj, J. Organometallics 2014, 10, 2588.
6. [6]
  Zhang, H.; Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L. RSC Adv. 2016, 6, 8465. doi: 10.1039/C5RA27500H
7. [7]
  Wei, W.; Zhang, C.; Xu Y.; Wan, X. Chem. Commun. 2011, 47, 10827. doi: 10.1039/c1cc14602e
8. [8]
  (a) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819. For recent reviews see: (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
9. [9]
  A recent review: Krylov, I. B.; Vil', V. A.; Terent'ev, A. O. Beilstein J. Org. Chem. 2015, 11, 92.
10. [10]
  Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384. doi: 10.1021/ol3013606
11. [11]
  Zhou, J.; Jin, C.; Li, X.; Su, W. RSC Adv. 2015, 5, 7232. doi: 10.1039/C4RA14586K
12. [12]
  Tran, B. L.; Driess, M.; Hartwig J. F. J. Am. Chem. Soc. 2014, 136, 17292. doi: 10.1021/ja510093x
13. [13]
  Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2014, 16, 2530. doi: 10.1021/ol5009119
14. [14]
  Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086. doi: 10.1021/ol5011906
15. [15]
  García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-Dorado, F. J.; Ortega, M. J.; Massanet, G. M.; Guerra, F. M. Org. Lett., 2014, 16, 1598. doi: 10.1021/ol500198c
16. [16]
  Koschker, P.; Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011, 28, 20746.
17. [17]
  Thiery, E.; Aouf, C.; Belloy, J.; Harakat, D.; Bras, J. L.; Muzart, J. J. Org. Chem. 2010, 75, 1771. doi: 10.1021/jo902587u
18. [18]
  Recent reviews, see: Chem. Rev. 2008, 109(8), all of the articles therein; also see: Suzuki, M. Acc. Chem. Res. 2007, 40, 609.
19. [19]
  We also reported a series of reactions about the ligand effects on copper, silver and gold catalysts: (a) Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395. (b) Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953. (c) Yu, M.; Wang, Y.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2009, 50, 6791. (d) Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett 2011, 2363. (e) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Adv. Synth. Catal. 2012, 354, 71. (f) Wang, Y.; Wu, C.; Nie, S.; Xu, D.; Yao, X. Tetrahedron Lett. 2015, 56, 6827.
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