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Copper-Catalyzed Double N-Vinylation of Aromatic Amines: An Efficient Synthesis of Various Substituted N-Arylpyrroles

  作者 LIAO QIAN; ZHANG LIYUN; WANG FEI; LI SHUTAO; XI CHANJUAN  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-28;  页码  5426-5431  
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[摘要]A simple and efficient approach to various substituted N-arylpyrroles has been developed The method is based on the copper-catalyzed sequential inter- and intramolecular N-vinylation of aromatic amines The reactions proceed to afford substituted N-arylpyrroles in good-to-excellent yields using CuI as the precatalyst, tBuONa as the base, and N-1,N-2-dimethylethane-1,2-diamine (DMEDA) as the ligand Airlines with electron-donating and -withdrawing substituents as well as a heteroaromatic amine performed very well under the conditions used. Tri- and tetrasubstituted dienyl diiodides also performed well under the reaction conditions and afforded the corresponding substituted N-arylpyrroles in good yields. Products were also obtained in high yields with CuBr or CuCl as precatalyst

 
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