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J Am Chem Soc. 2006 Apr 19;128(15):4972-3.

Room temperature palladium-catalyzed 2-arylation of indoles.

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Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, USA.


This communication describes the rational development of a PdII-catalyzed method for the direct 2-arylation of indoles using [Ar-IIII-Ar]BF4. These reactions proceed under remarkably mild conditions (often at room temperature and in the presence of ambient air and moisture), and these features are believed to be the result of a PdII/IV mechanism operating in these systems. These transformations can be used to prepare functionally diverse 2-arylated indoles and pyrroles, and their potential utility has been expanded by the development of an in situ procedure for generating the iodine(III) arylating reagents.

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