Palladium And Rhodium Catalyze The Application Of N-alkylation Of Alcohol Amines

N-alkylated amine is one of the key functional groups in organic chemistry. It plays a major role in the elaboration and composition of biological and chemical systems. N-alkylated amines are typically synthesized by using conventional alkylating agents, such as alkyl halides, however, this procedure can be problematic due to over-alkylation and the toxic nature of many alkyl halides and related alkylating agents. The use of alcohols instead of alkyl halides to achieve the N-alkylated amines is an attractive method because it produces only water as byproduct and does not need special equipment.The direct N-alkylation of amines with alcohols has emerged as a new green protocol to construct C-N bonds. This paper has the following components:Firstly, a very simple and convenient Pd/C catalytic system for the direct N-alkylation of amines with alcohols in pure water is developed. Based on this catalytic system, the factors for the N-alkylation reaction including reaction temperature, reaction time, bases, different solvents and reaction atmosphere are investigated. Experimental results suggested that the products containing C-N single bonds could be synthesized in 26%?100% yields using Pd/C and sodium hydroxide at 150? for 24 h. N-alkylation of amines with alcohols could be carried out in water and air. The products were characterized by 1HNMR, GC-MS and elemental analysis.Secondly, a stable, easily recoverable heterogeneous catalyst Ir-N@C (the mass fraction of iridium is 5%) is obtained by impregnation with commercial carbon powder. The factors of the N-alkylation reaction including different iridium catalysts, reaction temperature, reaction time and bases are investigated. Experiment results suggest that the N-alkylation of amines with primary alcohols could be efficiently catalyzed in water using iridium catalyst with n (Ir):n (1,10-Phenanthroline)= 1 2. In recycling experiments, the catalyst show acceptable stability and the catalytic activity is not obviously decreased. The catalyst is characterized by XRD, TEM, XPS, BET.