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Abstract We report a palladium-catalyzed allene bifunctionalization reaction that forms C C and either C O or C N bonds in one pot with excellent regio- and stereoselectivity. Carboxylic acids,… Click to show full abstract
Abstract We report a palladium-catalyzed allene bifunctionalization reaction that forms C C and either C O or C N bonds in one pot with excellent regio- and stereoselectivity. Carboxylic acids, amides, and hydroxide are all suitable nucleophiles. Organoboronic acid acts as hydroxide transfer reagent. An intermediate π-allyl palladium complex was isolated, which yields improved catalytic performance as well as evidence of the origin of stereoselectivity. A derivatization study emphasizes the utility of the functionalized allylic products.
Journal Title: Tetrahedron
Year Published: 2017
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