A variety of 1,5-diaryl-1H-imidazoles 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 mixture of Pd(OAc)2 and AsPh3. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium- (II) halide species onto the imidazole ring. Interestingly, some imidazole derivatives synthesized in this study have been found to exhibit significant cytotoxic activity against human tumor cell lines.

Regioselective Synthesis of 1,5-Diaryl-1H- imidazoles by Palladium-Catalyzed Direct Arylation of 1-Aryl-1H-imidazoles / F., Bellina; S., Cauteruccio; Mannina, Luisa; R., Rossi; S., Viel. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - 70:(2005), pp. 3997-4005. [10.1021/jo050274a]

Regioselective Synthesis of 1,5-Diaryl-1H- imidazoles by Palladium-Catalyzed Direct Arylation of 1-Aryl-1H-imidazoles

MANNINA, LUISA;
2005

Abstract

A variety of 1,5-diaryl-1H-imidazoles 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 mixture of Pd(OAc)2 and AsPh3. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium- (II) halide species onto the imidazole ring. Interestingly, some imidazole derivatives synthesized in this study have been found to exhibit significant cytotoxic activity against human tumor cell lines.
2005
Regioselective Synthesis
01 Pubblicazione su rivista::01a Articolo in rivista
Regioselective Synthesis of 1,5-Diaryl-1H- imidazoles by Palladium-Catalyzed Direct Arylation of 1-Aryl-1H-imidazoles / F., Bellina; S., Cauteruccio; Mannina, Luisa; R., Rossi; S., Viel. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - 70:(2005), pp. 3997-4005. [10.1021/jo050274a]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/47130
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