141136-36-9Relevant articles and documents
Direct synthesis of nitriles by Cu/DMEDA/TEMPO-catalyzed aerobic oxidation of primary amines with air
Ma, Xian-Tao,Xu, Hao,Xiao, Ying-Lin,Su, Chen-Liang,Liu, Jian-Ping,Xu, Qing
, p. 1336 - 1339 (2017/06/21)
By screening the copper catalysts, ligands, and the reaction conditions, a simple CuCl/DMEDA/TEMPO catalyst system readily available from commercial sources is developed for a direct and selective synthesis of the useful nitriles by an aerobic oxidation reaction of primary amines using air as an advantageous oxidant under mild conditions.
Heterogeneously catalyzed self-condensation of primary amines to secondary amines by supported copper catalysts
Kim, Insu,Itagaki, Shintaro,Jin, Xiongjie,Yamaguchi, Kazuya,Mizuno, Noritaka
, p. 2397 - 2403 (2013/09/02)
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.