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CuI/Proline-catalyzed N-Arylation of Nitrogen Heterocycles 被引量：2

CuI/Proline-catalyzed N-Arylation of Nitrogen Heterocycles
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摘要 Ma＇s CuI/proline procedure for the catalytic cross coupling between nitrogen heterocycles and aryl halides was markedly improved. The key finding was that K3PO4 was a much better base than K2CO3 for the reaction. With this new reaction condition the cross coupling with aryl iodides could be accomplished in 1,4-dioxane instead of DMSO. This reactin also could be carried out in DMF. Furthermore, the coupling yields under the new conditions are usually higher than in Ma＇s original methods. Ma＇s CuI/proline procedure for the catalytic cross coupling between nitrogen heterocycles and aryl halides was markedly improved. The key finding was that K3PO4 was a much better base than K2CO3 for the reaction. With this new reaction condition the cross coupling with aryl iodides could be accomplished in 1,4-dioxane instead of DMSO. This reactin also could be carried out in DMF. Furthermore, the coupling yields under the new conditions are usually higher than in Ma＇s original methods.
作者 Wei DENG Ye Feng WANG Chen ZHANG Lei LIU Qing Xiang GUO
机构地区 Department of Chemistry
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第3期313-316,共4页 中国化学快报（英文版）
关键词 Cross coupling reaction CUI N-ARYLATION nitrogen heterocycle proline. Cross coupling reaction, CuI, N-arylation, nitrogen heterocycle, proline.
分类号 O626 [理学—有机化学] O621.251 [理学—有机化学]
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参考文献8

  • 1[1](a) D.Z.Wang,L.H.Cao,Chem.Res.Chin.Univ.,2005,21,172.(b) G.Liu,B.A.Song,W.J.Sang,Y.Song,L.H.Jin,X.Ding,Chin.J.Org.Chem.,2004,24,1296.(c) D.S.Guo,Chin.J.Org.Chem.,2004,24,1118.(d) S.X.Li,Y.G.Wang,Chin.J.Org.Chem.,2003,23,1311.(e) Z.S.Lu,Z.P.Ni,D.Z.Niu,S.J.Tu,Chin.J.Org.Chem.,2003,23,89.
  • 2[2]D.Ma,Q.Cai,Synlett,2004,128.
  • 3[3]J.C.Antilla,J.M.Baskin,T.E.Barder,S.L.Buchwald,J.Org.Chem.,2004,69,5578.
  • 4[4]L.Xu,D.Zhu,F.Wu,R.Wang,B.Wan,Tetrahedron,2005,61,6553.
  • 5[5]For Ma's other Cu/amino acid catalysts,see:(a) D.Ma,Y.Zhang,J.Yao,S.Wu,F.Tao,J.Am.Chem.Soc.,1998,120,12459.(b) D.Ma,C.Xia,Org.Lett.,2001,3,2583.(c) D.Ma,Q.Cai,H.Zhang,Org.Lett.,2003,5,2453.(d) D.Ma,Q.Cai,Org.Lett.,2003,5,3799.(e) W.Zhu,D.Ma,Chem.Commun.,2004,888.(f) X.Pan,Q.Cai,D.Ma,Org.Lett.,2004,6,1809.(g) D.Ma,F.Liu,Chem.Commun.,2004,1934.(h) W.Zhu,D.Ma,J.Org.Chem.,2005,70,2696.(i) Q.Cai,W.Zhu,H.Zhang,Y.Zhang,D.Ma,Synthesis,2005,496.
  • 6[6]For our own Cu/amino acid catalysts,see:(a) W.Deng,Y.Zou,Y.F.Wang,L.Liu,Q.X.Guo,Synlett,2004,1254.(b) W.Deng,Y.F.Wang,Y.Zou,L.Liu,Q.X.Guo,Tetrahedron Lett.,2004,45,2311.(c) W.Deng,L.Liu,Q.X.Guo,Chin.J.Org.Chem.,2004,24,150.
  • 7[7]Typical experimental procedure for aryl iodide coupling:A mixture of aryl iodide (5.0 mmol),indole (6.0 mmol),K3PO4 (12.5 mmol),CuI (0.25 mmol),and L-proline (1.0 mmol) in 10 mL of dioxane was heated at 100 ℃ under nitrogen atmosphere for 24 h.The resulting suspension was cooled to room temperature and filtered through a 2-3 cm pad of silica gel with 100 mL of EtOAc.The filtrate was concentrated and the residue was purified by chromatography to afford the pure product.
  • 8[8]Typical experimental procedure for aryl bromide coupling:A mixture of aryl bromide (5.0 mmol),indole (6.0 mmol),K3PO4 (12.5 mmol),CuI (1.0 mmol),and L-proline (1.0 mmol) in 10 mL of DMF was heated at 140 ℃ under nitrogen atmosphere for 48 h.The resulting suspension was cooled to room temperature and filtered through a 2-3 cm pad of silica gel with 100 mL of EtOAc.The filtrate was concentrated and the residue was purified by chromatography to afford the pure product.

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Chinese Chemical Letters
2006年 第3期

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