Palladium-Catalyzed Direct C–H Arylation of Cyclic Enaminones with Aryl Iodides

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Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

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An oxidative boron-Heck reaction of cyclic enaminones with arylboronic acids is reported. This protocol provides a regioselective arylation at the C6 position of cyclic enaminones. When an N-carbamylated cyclic enaminone was employed, a switch to a conjugate addition reaction occurred in the presence of acid.

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ژورنال

عنوان ژورنال: The Journal of Organic Chemistry

سال: 2013

ISSN: 0022-3263,1520-6904

DOI: 10.1021/jo400830t