Copper-Mediated/Catalyzed Oxyalkylation of Alkenes with Alkylnitriles

A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (g-lactones) or isochromanones (d-lactones) via the formation of a C(sp3)C(sp3) and a C(sp3)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(sp3)C(sp3) bond rather than the C(sp3)O bond. Catalytic conditions were subsequently developed using carboxylic acid as an internal nucleophile.


Published in:
Chemistry - A European Journal, 20, 45, 14633-14636
Year:
2014
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2014-10-29, last modified 2018-12-03


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