Journal of Organic Chemistry p. 3359 - 3363 (1984)
Update date:2022-08-12
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Watanabe, Yoshihisa
Tsuji, Yasushi
Ige, Hitoshi
Ohsugi, Yukihiro
Ohta, Tetsuo
Aminoarenes were readily converted into secondary and tertiary amines by the reaction at 150-180 deg C with primary alcohols in the presence of a catalytic amount (1 mol percent based on the aminoarene) of a ruthenium complex.Dichlorotris(triphenylphosphine)ruthenium was the most effective catalyst precursor.Secondary amines were obtained in excellent yields when aminoarenes reacted with an equimolar amount of alcohols.With excess alcohols, tertiary amines were obtained predominantly.Kinetic measurements revealed that the rate had zero-order dependence on aminoarene concentration and first-order dependence on alcohol concentration and initial concentration of the ruthenium catalyst.From the kinetic features, the possible catalytic cycle, which includes the nucleophilic attack of the aminoarene on aldehyde intermediate, was postulated.
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