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Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles
Ala Bunescu1, Qian Wang, Jieping Zhu
1Laboratory 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).
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.
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