Organic & Biomolecular Chemistry 2008-12-21

A one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives activated by the combination of iodobenzene diacetate/iodine and iron dust.

Renhua Fan, Weixun Li, Bing Wang

Index: Org. Biomol. Chem. 6(24) , 4615-21, (2008)

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Abstract

An efficient one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives with electron-rich aromatic compounds is reported. The reaction is activated by the combination of iodobenzene diacetate, iodine and iron dust, resulting in a mild and simple reaction system. The use of iron avoids the oxidation of aromatic compounds, and in situ generation of Fe(III) salts to promote the Friedel-Crafts reaction avoids the use of the highly hygroscopic FeCl(3).