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Cu-catalyzed cross-couplings under ligandless conditions

Cu-catalyzed cross-couplings under ligandless conditions
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摘要 The possibility to carry out Cu-catalyzed cross-couplings under ligandless conditions was studied. It was found that by using K3PO4 as the base, the cross-coupling could proceed successfully between aryl iodides and several types of nucleophiles. Aryl bromides were completely inactive under the same reaction conditions. The possibility to carry out Cu-catalyzed cross-couplings under ligandless conditions was studied. It was found that by using K3PO4 as the base, the cross-coupling could proceed successfully between aryl iodides and several types of nucleophiles. Aryl bromides were completely inactive under the same reaction conditions.
作者 Chuan Zhou Tao Juan Li Xin Cui Yao Fu Qing Xiang Guo
机构地区 Department of Chemistry
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第10期1199-1202,共4页 中国化学快报（英文版）
关键词 CU CATALYSIS CROSS-COUPLING Ligand free Cu Catalysis Cross-coupling Ligand free
分类号 O643.3 [理学—物理化学]
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参考文献6

  • 1[1]Recent studies:(a) W.Deng,L.Liu,Q.X.Guo,Chin.J.Org.Chem.24 (2004) 150;(b)M.Sugahara,T.Ukita,Chem.Pharm.Bull.45 (1997) 719;(c)H.J.Cristau,P.P.Cellier,J.F.Spindler,M.Taillefer,Chem.Eur.J.10 (2004) 5607;(d)J.J.Yin,S.L.Buchwald,J.Am.Chem.Soc.124 (2002) 6043;(e)H.Rahman,T.Mahmood,M.Maryam,M.Hamidreza,Synlett (2004) 1575.
  • 2[2](a) D.Ma,Y.Zhang,J.Yao,S.Wu,F.Tao,J.Am.Chem.Soc.120 (1998) 12459;(b)J.C.Antilla,A.Klapars,S.L.Buchwald,J.Am.Chem.Soc.124 (2002) 11684.
  • 3[3]Our recent studies:(a) W.Deng,Y.F.Wang,Y.Zou,L.Liu,Q.X.Guo,Tetrahedron Lett.45 (2004) 2311;(b)W.Deng,Y.Zou,Y.F.Wang,L.Liu,Q.X.Guo,Synlett (2004) 1254;(c)X.H.Tan,C.Z.Tao,Y.Q.Hou,L.Luo,L.Liu,Q.X.Guo,Chin.J.Chem.23 (2005) 237;(d)W.Deng,L.Liu,C.Zhang,M.Liu,Q.X.Guo,Tetrahedron Lett.46 (2005) 7295;(e)Y.F.Wang,W.Deng,L.Liu,Q.X.Guo,Chin.Chem.Lett.16 (2005) 1197;(f)S.L.Zhang,L.Liu,Y.Fu,Q.X.Guo,Theochem 757 (2005) 37;(g)Y.F.Wang,Y.Zhou,J.R.Wang,Q.X.Guo,Chin.Chem.Lett.17 (2006) 1283;(h)W.Deng,Y.F.Wang,L.Liu,Q.X.Guo,Chin.Chem.Lett.17 (2006) 595;(I)W.Deng,Y.F.Wang,C.Zhang,L.Liu,Q.X.Guo,Chin.Chem.Lett.17 (2006) 313;(j)Y.F.Wang,Y.Zhou,J.R.Wang,L.Liu,Q.X.Guo,Chin.Chem.Lett.18 (2007) 499;(k)C.Z.Tao,X.Cui,J.Li,A.X.Liu,L.Liu,Q.X.Guo,Tetrahedron Lett.48 (2007) 3525.
  • 4[4]Some examples:(a) G.W.Kabalka,L.Wang,Tetrahedron Lett.43 (2002) 3067;(b)G.A.Molander,B.Biolatto,Org.Lett.4 (2002) 1867;(c)W.J.Liu,Y.X.Xie,Y.Liang,J.H.Li,Synthesis (2006) 860;(d)L.H.Du,Y.G.Wang,Synth.Commun.37 (2007) 217;(e)J.R.Wang,C.T.Yang,L.Liu,Q.X.Guo,Chin.Chem.Lett.18 (2007) 133.
  • 5[5]Typical experimental procedure for ligand-free Cu-catalyzed cross-couplings:an over-dried flask was charged with CuI (5.0 mol%),amide(1.2 mmol),and K3PO4 (3.0 mmol).The flask was filled with nitrogen and aryl iodide (1.0 mmol) was added,then solvent (2.0 mL) was added under nitrogen.The reaction mixture was sealed and stirred for 24 h at 110 ℃.The resulting suspension was cooled to room temperature and filtered through a pad of silica gel with the help of 100 mL of ethyl acetate.The filtrate was concentrated and the residue was purified by chromatography to afford the pure product.
  • 6[6]Y.Jin,J.Liu,Y.Yin,H.Fu,Y.Jiang,Y.Zhao,Synlett (2006) 1564.
Chinese Chemical Letters
2007年 第10期

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