Citation: An Yanni, Li Jianxiao, Zhang Zhenming, Li Chunsheng, Yang Shaorong. Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2136-2141. doi: 10.6023/cjoc201603043 shu

Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids

1.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Corresponding author: Yang Shaorong, lisryang@scut.edu.cn
Received Date: 27 March 2016
Revised Date: 14 April 2016

Fund Project: the National Natural Science Foundation of China 21502055the National Natural Science Foundation of China 2015ZM150China Postdoctoral Science Foundation 2015M572303

An efficient and practical palladium-catalyzed cascade oxidative heterocyclization has been developed to afford functionalized oxygen-containing five-membered heterocycles in moderate to good yields with high regio-and diastereo-selectivities. Their structures were confirmed by IR, ¹H NMR, ¹³C NMR and HRMS. Furthermore, the current methodology could also be conveniently applied to the synthesis of naturally occurring biologically active functionalized tetrahydrofurans and γ-lactones frameworks.
- palladium-catalyzed,
- ionic liquids,
- alkynes,
- alkenes,
- heterocycles
1. [1]
  Eftekhari-Sis, B.; Zirak, M.; Akbari, A.Chem.Rev.2013, 113, 2958.
  (b) Luo, P.; Tang, R.; Zhong, P.; Li, J.Chin.J.Org.Chem.2009, 29, 1924(in Chinese).
  (罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.)
2. [2]
  Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J.Chem.Rev.2015, 115, 5301.
  (b) Huang, H.; Ji, X.; Wu, W.; Jiang, H.Chem.Soc.Rev.2015, 44, 1155.
3. [3]
  Yang, L.; Huang, H.Chem.Rev.2015, 115, 3468.
  (b) Yamamoto, Y.Chem.Soc.Rev.2014, 43, 1575.
4. [4]
  Wu, W.; Jiang, H.Acc.Chem.Res.2012, 45, 1736.
  (b) Wu, W.; Jiang, H.Acc.Chem.Res.2014, 47, 2483.
5. [5]
  Su, D.; Tang, W.; Hu, Y.; Liu, Y.; Yu, S.; Ma, S.; Qu, J.; Yu, D.J.Nat.Prod.2008, 71, 784.
  (b) Chen, L.; Zhu, H.; Wang, R.; Zhou, K.; Jing, Y.; Qiu, F.J.Nat.Prod.2008, 71, 852.
6. [6]
  Liu, G.; Lu, X.Tetrahedron Lett.2003, 44, 127.
  (b) Son, S.; Fu, G.C.J.Am.Chem.Soc.2007, 129, 1046.
  (c) Huang, L.; Jiang, H.; Qi, C.; Liu, X.J.Am.Chem.Soc.2010, 132, 17652.
  (d) Huang, H.; Ji, X.; Wu, W.; Jiang, H.Chem.Commun.2013, 49, 3351.
  (e) Oliveira, C.C.; Angnes, R.A.; Correia, C.R.D.J.Org.Chem.2013, 78, 4373.
7. [7]
  Zhang, Q.; Xu, W.; Lu, X.J.Org.Chem.2005, 70, 1505. doi: 10.1021/jo048414o
8. [8]
  Wang, Z.; Lu, X.J.Org.Chem.1996, 61, 2254. doi: 10.1021/jo9522466
9. [9]
  Aurrecoechea, J.; Durana, A.; Pérez, E.J.Org.Chem.2008, 73, 3650. doi: 10.1021/jo800211q
10. [10]
  Martınez, C.; Álvarez, R.; Aurrecoechea, J.M.Org.Lett.2009, 11, 1083. doi: 10.1021/ol8028687
11. [11]
  Wolfe, J.P.; Rossi, M.J.Am.Chem.Soc.2004, 126, 1620.
  (b) Nakhla, J.; Kampf, J.; Wolfe, J.P.J.Am.Chem.Soc.2006, 128, 2893.
  (c) Lemen, G.S.; Giampietro, N.C.; Hay, M.B.; Wolfe, J.P.J.Org.Chem.2009, 74, 2533.
12. [12]
  Huang, L.; Wang, Q.; Liu, X.; Jiang, H.Angew.Chem., Int.Ed.2012, 51, 5696. doi: 10.1002/anie.201109141
13. [13]
  Huang, L.; Wang, Q.; Wu, W.; Jiang, H.J.Org.Chem.2014, 79, 7734. doi: 10.1021/jo501317v
14. [14]
  Zhang, Z.; Ouyang, L.; Wu, W.; Li, J.; Zhang, Z.; Jiang, H.J.Org.Chem.2014, 79, 10734. doi: 10.1021/jo501606c
15. [15]
  Zhang, Z.; Wu, W.; Liao, J.; Li, J.; Jiang, H.Chem.Eur.J.2015, 21, 6708. doi: 10.1002/chem.201500397
16. [16]
  Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sun, Y.; Jiang, H.Angew.Chem., Int.Ed.2014, 53, 7219. doi: 10.1002/anie.201403341
17. [17]
  Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J.J.Org.Chem.2013, 78, 12477.
  (b) Li, J.; Yang, S.Chin.J.Org.Chem.2013, 33, 2407(in Chinese).
  (李建晓, 杨少容, 有机化学, 2013, 33, 2407.)
  (c) Li, J.; Yang, S.; Wu, W.; Jiang, H.Chem.Commun.2014, 50, 1381.
  (d) Li, J.; Li, C.; Yang, S.; Luo, W.Chin.J.Org.Chem.2015, 35, 898(in Chinese).
  (李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.)
  (e) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H.J.Org.Chem.2015, 80, 3870.
  (f) Li, J.; Zhang, Z.; Li, C.; Luo, W.; Yang, S.Chin.J.Org.Chem.2015, 35, 2199(in Chinese).
  (李建晓, 张振明, 李春生, 罗维, 杨少容, 有机化学, 2015, 35, 2199.)
18. [18]
  Huddleston, J.G.; Willauer, H.D.; Swatloski, R.P.; Visser, A.E.; Rogers, R.D.Chem.Commun.1998, 1765.
19. [19]
  Park, S.; Kazlauskas, R.J.J.Org.Chem.2001, 66, 8395. doi: 10.1021/jo015761e
20. [20]
  Branco, L.C.; Rosa, J.N.; Ramos, J.J.M.; Afonso, C.A.M.Chem.Eur.J.2002, 8, 3671. doi: 10.1002/1521-3765(20020816)8:16<3671::AID-CHEM3671>3.0.CO;2-9
21. [21]
  Miao, C.X.; He, L.N.; Wang, J.Q.; Wang, J.L.Adv.Synth.Catal.2009, 351, 2209. doi: 10.1002/adsc.v351:13
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沈阳化工大学材料科学与工程学院沈阳 110142