Efficient Cross‐Coupling Reactions of Nitrogen Nucleophiles with Aryl Halides in Water

Yong‐Chua Teo

doi:10.1002/adsc.200800746

Efficient Cross‐Coupling Reactions of Nitrogen Nucleophiles with Aryl Halides in Water

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Yong‐Chua Teo

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<jats:title>Abstract</jats:title><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/mcontent.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text></jats:p><jats:p>A facile and practical strategy has been developed for the <jats:italic>N</jats:italic>‐arylation of nitrogen nucleophiles with aryl halides catalyzed by a combination of iron(III) chloride [FeCl<jats:sub>3</jats:sub>] and dimethylethylenediamine (dmeda) in water. A variety of nitrogen nucleophiles including pyrazole, indole, 7‐azaindole and benzamide afforded the <jats:italic>N</jats:italic>‐arylated products in the presence of the catalytic system (in up to 88% yield).</jats:p>