We have developed a mild and efficient palladium(II)-catalyzed oxidative diarylating carbocyclization of enynes (Scheme 1). This reaction shows tolerance of a range of functionalized arylboronic acids and converts simple acyclic O-tethered enynes into diarylated heterocycles (tetrahydrofurans and tetrahydropyrans) in good yields. Control experiments suggest that the oxygen-tether is crucial allowing the reaction to initiate with an arylpalladation of the alkyne, followed by cis-migratory insertion (carbocyclization), transmetallation and reductive elimination to give the diarylated product.

Palladium-catalyzed oxidative diarylating carbocyclization of enynes

245th National Meeting (2013)

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