Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparation. In this paper, we report a direct cross-coupling reaction of heteroarenes with N,N-dimethylanilines in the presence of copper catalyst. Oxygen and/or air are successfully used as the oxidant, which is of great importance to the industrialized economies. The reaction is compatible with a wide range of heterocycles, including indolizines, imidazoles, indoles, and aniline, to enable the formation of various alkylated heteroarenes under very mild reaction conditions.
A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N'-dimethylethane-1,2-diamine (DMEDA).
An efficient iron-promoted alkylation of indoles with enamides has been accomplished under mild reaction conditions. The reaction proceeded with remarkable regioselectivity leading exclusively to substitution by indoles at α-position of enamides.
A two-step modular synthesis of an α-hydroxycyclopentenone and α-amido-indanones has been developed based on the Nazarov cyclization of 2-amido-1,4-pentadien-3-ones, readily accessed via formal hydroacylation of allenamides.
FeCl 3 -Promoted Alkylation of Indoles by Enamides. -The Fe(III)-catalyzed addition of indole derivatives towards enamides can afford either mono-(III) or bisadducts (VII) depending on the amount of indole used. Interestingly, the formation of unsymmetrical bisindolylmethanes like (VI) is smoothly achieved. The method can be extended to indolizidines (VIII). -(NIU, T.; HUANG, L.; WU, T.; ZHANG*, Y.; Org. Biomol. Chem. 9 (2011) 1, 273-277, http://dx.
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