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A General approach to substituted benzimidazoles and benzoxazoles via heterogeneous palladium-catalyzed hydrogen-transfer with primary amines

Pizzetti, Marianna and De Luca, Elisa and Petricci, Elena and Porcheddu, Andrea and Taddei, Maurizio (2012) A General approach to substituted benzimidazoles and benzoxazoles via heterogeneous palladium-catalyzed hydrogen-transfer with primary amines. Advanced Synthesis & Catalysis, Vol. 354 (13), p. 2453-2464. eISSN 1615-4169. Article.

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DOI: 10.1002/adsc.201200253

Abstract

The synthesis of benzimidazoles starting from o-phenylenediamines and amines in the presence of palladium on charcoal as catalyst is reported. Under microwave dielectric heating it is possible to use a tertiary, a secondary, and even a primary amine as the substrate for a palladium-mediated process to get 2-substituted or 1,2-disubstituted benzimidazoles, depending on the nature of the o-phenylenediamine employed. Primary amines are the most suitable reagents for the atom economy of the overall process that resulted to be general as several different substituted benzimidazoles were obtained in good yield. Benzoxazoles can be also prepared starting from primary amines and o-aminophenol. The reaction is also highly selective as no (poly)-alkylated pheny- lenediamines or cross-contaminated benzimidazoles are obtained starting from N-monoalkylphenylenediamines. This behavior was interpreted as a scarce aptitude to dehydrogenation of the methylene bonded to the aromatic NH of N-alkylarylamines. The experiments carried out consent to draw an almost complete picture of the reaction pathways occurring during the process. The catalyst can be recycled several times and, although far from optimal performances, catalyst TON=90 is encouraging for further large-scale optimization protocols. In addition, the palladium on charcoal-catalyzed microwave-assisted reaction of o-phenylenediamine gives de-alkylation of tertiary amines and transformation into the secondary ones.

Item Type:Article
ID Code:8087
Status:Published
Refereed:Yes
Uncontrolled Keywords:Amines, heterocycles, heterogeneous catalysis, hydrogen transfer, microwave chemistry
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Wiley
eISSN:1615-4169
Deposited On:23 Oct 2012 13:33

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