Regioselective Arylation Reactions of Biphenyl-2-ols, Naphthols, and Benzylic Compounds with Aryl Halides under Palladium Catalysis

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Abstract
Biphenyl-2-ols undergo regioselective mono- and diarylation upon a treatment with aryl iodides in the presence of a palladium catalyst in DMF using Cs2CO3 as a base to produce 1,1′ : 2′,1″-terphenyl-2-ol and 2′,6′-diphenylbiphenyl-2-ol and their derivatives. The reaction of 1-naphthol selectively occurs at its 8-position to give 8-aryl-1-naphthols. In the reaction of 2-naphthol with aryl bromides, diarylated compounds, 1-(2-arylphenyl)-2-naphthols, are formed as the single major products. Under similar conditions, benzyl ketones, phenylacetonitrile, and methyl phenylacetate are arylated at their benzylic position.