Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 18, Pages 7793-7803Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3014275
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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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