title: Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles.
abstract: A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (γ-lactones) or isochromanones (δ-lactones) via the formation of a C(sp(3) )C(sp(3) ) and a C(sp(3) )O bond with the generation of up to two quaternary carbon atoms. Mechanistic studies suggest that this reaction is initiated by the formation of the C(sp(3) )C(sp(3) ) bond rather than the C(sp(3) )O bond. Catalytic conditions were subsequently developed using carboxylic acid as an internal nucleophile.
authors.affiliation: Laboratory of Synthesis and Natural Product, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland).
authors.forename: Ala
authors.initials: A
authors.lastname: Bunescu
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
keywords: alkenes; alkylation; copper; lactones; oxyalkylation