Cyanoesterification of 1,2-Dienes: Synthesis and Transformations of Highly Functionalized α-Cyanomethylacrylate Esters
Journal of the American Chemical Society2006Vol. 128(23), pp. 7420–7421
Citations Over TimeTop 10% of 2006 papers
Abstract
A Ni/PMe2Ph catalyst is found to effect regioselective addition of cyanoformate esters across 1,2-dienes, giving rise to 3-alkoxycarbonyl-3-butenenitriles. Functional groups such as cyano, protected hydroxyl, and amino groups in the 1,2-diene substrates are tolerated. Isomerization of the initial products to thermodynamically more stable isomers takes place possibly through further oxidative addition of the C-CN bond of 3-alkoxycarbonyl-3-butenenitriles to Ni(0) followed by reductive elimination. The cyanoesterification products undergo further addition across alkynes in the presence of a Ni/P(4-CF3-C6H4)3 catalyst.
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