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A palladium iodide-catalyzed oxidative aminocarbonylation–heterocyclization approach to functionalized benzimidazoimidazoles

A palladium iodide-catalyzed oxidative aminocarbonylation–heterocyclization approach to functionalized benzimidazoimidazoles

Veltri, Lucia, Giofrè, Salvatore V., Devo, Perry, Romeo, Roberto, Dobbs, Adrian P. and Gabriele, Bartolo (2018) A palladium iodide-catalyzed oxidative aminocarbonylation–heterocyclization approach to functionalized benzimidazoimidazoles. Journal of Organic Chemistry, 83. pp. 1680-1685. ISSN 0022-3263 (Print), 1520-6904 (Online) (doi:10.1021/acs.joc.7b03167)

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Abstract

A novel carbonylative approach to the synthesis of functionalized 1H-benzo[d]imidazo[1,2-a]imidazoles is presented. The method consists of the oxidative aminocarbonylation of N-substituted-1-(prop-2-yn-1-yl)-1H-benzo[d]imidazol-2-amines, carried out in the presence of secondary nucleophilic amines, to give the corresponding alkynylamide intermediates, followed by in situ conjugated addition and double-bond isomerization, to give 2-(1-alkyl-1H-benzo[d]imidazo[1,2-a]imidazol-2-yl)acetamides. Products were obtained in good to excellent yields (64–96%) and high turnover numbers (192–288 mol of product per mol of catalyst) under relatively mild conditions (100 °C under 20 atm of a 4:1 mixture of CO–air), using a simple catalytic system, consisting of PdI2 (0.33 mol %) in conjunction with KI (0.33 equiv).

Item Type: Article
Uncontrolled Keywords: Heterocyclic chemistry palladium catalysis aminocarbonylation Benzimidazoimidazoles
Subjects: Q Science > QC Physics
Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Last Modified: 30 Apr 2018 10:52
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: GREAT a
URI: http://gala.gre.ac.uk/id/eprint/19205

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