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Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones for the Synthesis of 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones

  作者 ALJAAR NAYYEF; MALAKAR CHANDI C; CONRAD JUERGEN; STROBEL SABINE; SCHLEID THOMAS; BEIFUSS UWE  
  选自 期刊  Journal of Organic Chemistry;  卷期  2012年77-18;  页码  7793-7803  
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[摘要]The Cu(I)-catalyzed reaction of 1-bromo-2-iodobenzenes and other 1,2-dihalobenzenes with 1,3-cyclohexanediones in DMF at 130 degrees C using Cs2CO3 as a base and pivalic acid as an additive selectively delivers 3,4-dihydrodibenzo [b,ci] furan-1(2H)-ones with yields ranging from 47 to 83%. The highly regioselective domino process is based on an intermolecular Ullmann-type C-arylation followed by an intramolecular Ullmann-type O-arylation. Substituted products are accessible by employing substituted 1-bromo-2-iodobenzenes and substituted 1,3-cyclohexanediones as substrates. Reaction with an acyclic 1,3-diketone yields the corresponding benzo[b]furan.

 
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