Tetrahedron
Tetrahedron
4 years ago

Highly regio- and stereoselective palladium-catalyzed allene bifunctionalization cascade via π-allyl intermediate

Highly regio- and stereoselective palladium-catalyzed allene bifunctionalization cascade via π-allyl intermediate
We report a palladium-catalyzed allene bifunctionalization reaction that forms CC and either CO or CN 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.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017308529

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