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ABSTRACT: Benzimidazoles were synthesized by the copper-catalyzed, one-pot, three-component reaction of 2-haloanilines, aldehydes, and NaN(3). The reaction was optimized when 2-iodo- or 2-bromoanilines (1.0 equiv), aldehydes (1.2 equiv), NaN(3) (2.0 equiv), 5 mol% of CuCl, and 5 mol % of TMEDA were reacted in DMSO at 120 °C for 12 h. Good yields resulted, and the reaction showed tolerance toward functional groups such as ester, nitro, and chloro. Aliphatic and heteroaromatic aldehydes also afforded the desired products in moderate to good yields.
The Journal of Organic Chemistry 12/2011; 76(23):9577-83. · 4.45 Impact Factor
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Angewandte Chemie International Edition 05/2011; 50(19):4386-9. · 13.45 Impact Factor
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Tetrahedron Letters 01/2011; · 2.68 Impact Factor
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Tetrahedron Letters 01/2011; · 2.68 Impact Factor
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ABSTRACT: Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from phenyl propiolic acid without any formation of a noncarbonylative coupling product in the absence of CuI. However, the reaction with alkyl-substituted alkynyl carboxylic acids required CuI as a cocatalyst for high yield.
Organic Letters 01/2011; 13(5):944-7. · 5.86 Impact Factor