Journal of the American Chemical Society 2006-04-19

Room temperature palladium-catalyzed 2-arylation of indoles.

Nicholas R Deprez, Dipannita Kalyani, Andrew Krause, Melanie S Sanford

Index: J. Am. Chem. Soc. 128(15) , 4972-3, (2006)

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Abstract

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.