Catalysis science and technology p. 2397 - 2403 (2013)
Update date:2022-08-04
Topics: Reaction Time Product Analysis Catalyst Loading Primary Amines Secondary Amines Reactor Reaction temperature Heterogeneously catalyzed Self-condensation Supported copper catalysts Pressure
Kim, Insu
Itagaki, Shintaro
Jin, Xiongjie
Yamaguchi, Kazuya
Mizuno, Noritaka
Self-condensation of primary amines to symmetrically substituted secondary amines could efficiently be promoted by an inexpensive supported copper catalyst, Cu/Al2O3, easily prepared by the reduction of the hydroxide precursor, Cu(OH)x/Al2O3. Various kinds of structurally diverse primary amines including benzylamine, picolylamine, and aliphatic amine derivatives could selectively be converted into the corresponding secondary amines in moderate to excellent yields without any cocatalysts such as bases and stabilizing ligands in 1 atm of Ar or H 2. The reactions in H2 showed higher selectivities to desired secondary amines than those in Ar. The roles of H2 are the promotion of hydrogenation of N-alkylimines and the stabilization of active Cu(0) species. In addition, in the presence of Cu/Al2O3, unsymmetrically substituted secondary amines could efficiently be synthesized by N-alkylation of primary amines with alcohols and reductive amination of aldehydes. The observed catalysis was truly heterogeneous, and the retrieved Cu/Al2O3 catalyst could be reused for self-condensation without a significant loss of its catalytic performance. The reaction mechanism involving dehydrogenation of primary amines and condensation to N-alkylimines followed by hydrogenation, the so-called "borrowing hydrogen pathway", has been proposed. The Royal Society of Chemistry 2013.
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Doi:10.1016/S0957-4166(00)82085-6
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(2013)