Allylcyanation of alkynes: Regio- and stereoselective access to functionalized di- or trisubstituted acrylonitriles
2006
Allyl cyanides are found to add across alkynes in the presence of a nickel catalyst prepared from Ni(cod)2 and P(4-CF3−C6H4)3 in situ to give variously functionalized di- or trisubstituted acrylonitriles in highly stereoselective manners possibly via a π-allylnickel species as an intermediate. α-Siloxyallyl cyanides also react at the γ-position of a cyano group with both internal and terminal alkynes having various functional groups to give silyl enol ethers, which give the corresponding aldehydes or ketones upon hydrolysis.
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