ARTICLE

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

  • An Yanni ,
  • Li Jianxiao ,
  • Zhang Zhenming ,
  • Li Chunsheng ,
  • Yang Shaorong
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  • School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Received date: 2016-03-27

  Revised date: 2016-04-14

  Online published: 2016-05-17

Supported by

Project supported by the National Natural Science Foundation of China (No.21502055), the Fundamental Research Funds for the Central Universities (No.2015ZM150) and China Postdoctoral Science Foundation (No.2015M572303).

Abstract

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.

Cite this article

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

References

[1] (a) 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] (a) 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] (a) Yang,L.;Huang,H.Chem.Rev.2015,115,3468. (b) Yamamoto,Y.Chem.Soc.Rev.2014,43,1575.
[4] (a) Wu,W.;Jiang,H.Acc.Chem.Res.2012,45,1736. (b) Wu,W.;Jiang,H.Acc.Chem.Res.2014,47,2483.
[5] (a) 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] (a) 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] Zhang,Q.;Xu,W.;Lu,X.J.Org.Chem.2005,70,1505.
[8] Wang,Z.;Lu,X.J.Org.Chem.1996,61,2254.
[9] Aurrecoechea,J.;Durana,A.;Pérez,E.J.Org.Chem.2008,73,3650.
[10] Mart?nez,C.;Álvarez,R.;Aurrecoechea,J.M.Org.Lett.2009,11,1083.
[11] (a) 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] Huang,L.;Wang,Q.;Liu,X.;Jiang,H.Angew.Chem.,Int.Ed.2012,51,5696.
[13] Huang,L.;Wang,Q.;Wu,W.;Jiang,H.J.Org.Chem.2014,79,7734.
[14] Zhang,Z.;Ouyang,L.;Wu,W.;Li,J.;Zhang,Z.;Jiang,H.J.Org.Chem.2014,79,10734.
[15] Zhang,Z.;Wu,W.;Liao,J.;Li,J.;Jiang,H.Chem.Eur.J.2015,21,6708.
[16] Li,J.;Yang,W.;Yang,S.;Huang,L.;Wu,W.;Sun,Y.;Jiang,H.Angew.Chem.,Int.Ed.2014,53,7219.
[17] (a) 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] Huddleston,J.G.;Willauer,H.D.;Swatloski,R.P.;Visser,A.E.;Rogers,R.D.Chem.Commun.1998,1765.
[19] Park,S.;Kazlauskas,R.J.J.Org.Chem.2001,66,8395.
[20] Branco,L.C.;Rosa,J.N.;Ramos,J.J.M.;Afonso,C.A.M.Chem.Eur.J.2002,8,3671.
[21] Miao,C.X.;He,L.N.;Wang,J.Q.;Wang,J.L.Adv.Synth.Catal.2009,351,2209.

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