A variety of 1,5-diaryl-1H-imidazoles, e.g., I, have been regioselectively synthesized by direct coupling of 1-aryl-1H-imidazoles with aryl iodides or bromides in DMF in the presence of CsF as the base and a catalyst precursor consisting of a mixt. of Pd(OAc)2 and AsPh3. The data obtained support a reaction mechanism involving an electrophilic attack of an arylpalladium(II) halide species onto the imidazole ring. Interestingly, some of the imidazole derivs. have been found to exhibit significant cytotoxic activity against human tumor cell lines.
Regioselective synthesis of 1,5- and 1,2-diaryl-1H-imidazoles by Pd- or Pd/Cu-mediated direct arylation of 1-aryl-1H-imidazoles / F. Bellina, S. Cauteruccio, L. Mannina, R. Rossi, S. Viel. ((Intervento presentato al 13. convegno International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis tenutosi a Geneve nel 2005.
Regioselective synthesis of 1,5- and 1,2-diaryl-1H-imidazoles by Pd- or Pd/Cu-mediated direct arylation of 1-aryl-1H-imidazoles
S. Cauteruccio;
2005
Abstract
A variety of 1,5-diaryl-1H-imidazoles, e.g., I, have been regioselectively synthesized by direct coupling of 1-aryl-1H-imidazoles with aryl iodides or bromides in DMF in the presence of CsF as the base and a catalyst precursor consisting of a mixt. of Pd(OAc)2 and AsPh3. The data obtained support a reaction mechanism involving an electrophilic attack of an arylpalladium(II) halide species onto the imidazole ring. Interestingly, some of the imidazole derivs. have been found to exhibit significant cytotoxic activity against human tumor cell lines.
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