Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 14-15, Pages 2463-2473Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000493
Keywords
diazo compounds; Heck reaction; homogeneous catalysis; palladium; phenols
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Significantly better yields were achieved in Mizoroki-Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation-diazotation-precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C-C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.
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