Citation: Zhang Fusong, Lai Qi, Shi Xiaodong, Song Zhiguang. Triazole-gold (TAAu) catalyzed three-component coupling (A3 reaction) towards the synthesis of 2, 4-disubstituted quinoline derivatives[J]. Chinese Chemical Letters, ;2019, 30(2): 392-394. doi: 10.1016/j.cclet.2018.05.036 shu

Triazole-gold (TAAu) catalyzed three-component coupling (A3 reaction) towards the synthesis of 2, 4-disubstituted quinoline derivatives

Zhang Fusong ^a ,
Lai Qi ^a ,
Shi Xiaodong ^b,*, ,
Song Zhiguang ^a,*,

a.
Department of Chemistry, Jilin University, Changchun, Jilin 130021, China
b.
Department of Chemistry, University of South Florida, Tampa FL33620, United States

xmshi@usf.edu

szg@jlu.edu.cn

Received Date: 22 March 2018
Revised Date: 9 May 2018
Accepted Date: 22 May 2018
Available Online: 24 February 2018

Figures(2)

A gold-catalyzed three-component coupling reaction (A3 reaction) was developed as an efficient approach for the synthesis of challenging 2, 4-disubstituted quinoline derivatives. Compared to previously reported Cu/Au bi-catalyst system, this protocol enables achieving A3 reaction only in the presence of triazole-gold catalyst. Notably, 4-alkyl substituted or 2-alkyl substituted quinoline derivatives were obtained with good yields, which highlighted the unique advantage of this new strategy.
- Quinoline,
- Gold catalysis,
- A3 reaction,
- Triazole-gold
1. [1]
  H.Bienaymé, C.Hulme, G.Oddon, P.Schmitt, Chem.Eur.J.6(2000) 3321-3329.
2. [2]
  L.F.Tietze, Chem.Rev.96(1996) 115-136. doi: 10.1021/cr950027e
3. [3]
  C.Wei, Z.Li, C.J.Li, Org.Lett.5(2003) 4473-4475. doi: 10.1021/ol035781y
4. [4]
  C.M.Wei, Z.G.Li, C.J.Li, Synlett (2004) 1472-1483.
5. [5]
  V.A.Peshkov, O.P.Pereshivko, E.V.Van der Eycken, Chem.Soc.Rev.41(2012) 3790-3807. doi: 10.1039/c2cs15356d
6. [6]
  F.Xiao, Y.Chen, Y.Liu, J.Wang, Tetrahedron 64(2008) 2755-2761. doi: 10.1016/j.tet.2008.01.046
7. [7]
  P.Y.Chung, Z.X.Bian, H.Y.Pun, et al., Future Med.Chem.7(2015) 947-967. doi: 10.4155/fmc.15.34
8. [8]
  V.R.Solomon, H.Lee, Curr.Med.Chem.18(2011) 1488-1508. doi: 10.2174/092986711795328382
9. [9]
  D.J.Gorin, F.D.Toste, Nature 446(2007) 395-403. doi: 10.1038/nature05592
10. [10]
  S.Sengupta, X.D.Shi, ChemCatChem 2(2010) 609-619. doi: 10.1002/cctc.201000070
11. [11]
  D.Pflasterer, A.S.K.Hashmi, Chem.Soc.Rev.45(2016) 1331-1367. doi: 10.1039/C5CS00721F
12. [12]
  A.Furstner, Chem.Soc.Rev.38(2009) 3208-3221. doi: 10.1039/b816696j
13. [13]
  K.M.Jiang, J.A.Kang, Y.Jin, J.Lin, Org.Chem.Front.5(2018) 434-441. doi: 10.1039/C7QO00637C
14. [14]
  S.Hosseyni, C.A.Smith, X.Shi, Org.Lett.18(2016) 6336-6339. doi: 10.1021/acs.orglett.6b03228
15. [15]
  H.F.Duan, S.Sengupta, J.L.Petersen, N.G.Akhmedov, X.D.Shi, J.Am.Chem.Soc.131(2009) 12100. doi: 10.1021/ja9041093
16. [16]
  Y.F.Chen, W.M.Yan, N.G.Akhmedov, X.D.Shi, Org.Lett.12(2010) 344-347. doi: 10.1021/ol902680k
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142