Transition metal-catalyzed addition of amines to acrylic acid derivatives.A high-throughput method for evaluating hydroamination of primary and secondary alkylamines
M. Kawatsura et Jf. Hartwig, Transition metal-catalyzed addition of amines to acrylic acid derivatives.A high-throughput method for evaluating hydroamination of primary and secondary alkylamines, ORGANOMETAL, 20(10), 2001, pp. 1960-1964
Several new classes of transition metal-catalyzed reactions of amines with
the C=C bond of acrylic acid derivatives were discovered using a high-throu
ghput colorimetric assay. This assay is general for the reactions of primar
y and secondary alkylamines with acrylic acid derivatives, and the screenin
g of potential catalysts using this assay revealed a number of different me
tal/ligand combinations that promote these hydroaminations. The colorimetri
c assay revealed catalysts for the addition of piperidine to methacrylonitr
ile, crotononitrile, ethyl crotonate, and ethyl methacrylate, as well as ca
talysts for reactions of butylamine and aniline with methacrylonitrile. A c
atalyst for the addition of aniline to crotononitrile at 100 degreesC was a
lso discovered. The products of these reactions are basic building blocks f
or the synthesis of beta -amino acids, amino alcohols, and diamines. These
reactions may ultimately produce an enantioselective route to optically act
ive difunctional materials from commodity reagents.