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Relevant academic research and scientific papers

Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines

Triglycerides are used for the direct N-alkylation of amines with molecular hydrogen for the first time. A broad range of interesting and industrially relevant secondary and tertiary amines are obtained in the presence of an in situ formed Ru/Triphos complex. Notably, plant oil can be efficiently applied in this single-step process. Moreover, a variety of other methyl esters can be used as N-alkylation agents in the presence of hydrogen for the synthesis of more advanced building blocks.

Titanium complexes supported by imidazo[1,5-a]pyridine-containing pyrrolyl ligand as catalysts for hydroamination and polymerization reactions, and as an antitumor reagent

A new imidazo[1,5-a]pyridine-containing pyrrolyl ligand HL (HL = 3-(1H-pyrrol-2-yl)imidazo[1,5-a]pyridine) was synthesized and employed in the organometallic chemistry of titanium. The syntheses, structures, catalytic properties and antitumor activity of three titanium complexes supported by HL are reported. Reactions of Ti(NMe2)4 and Ti(NEt2)4 with 2 equivalents of HL, led to the production of titanium bisamido complexes TiL2(NMe2)2 (1) and TiL2(NEt2)2 (2), respectively. Treatment of Ti(OiPr)4 with 2 equivalents of HL resulted in the formation of TiL2(OiPr)2 (3). All complexes were characterized by elemental analyses and NMR studies. The solid-state structures of 2 and 3 were further established by single X-ray crystallography. The titanium bisamido complexes 1 and 2 are shown to be good pre-catalysts for the hydroamination of alkynes. Complex 1 was found to be an active catalyst for the ring-opening polymerization of ε-caprolactone. The cytotoxicity activities of 3 towards the tumor cells HCT-116, PC3 and MCF-7 were measured. Complex 3 exhibited good antitumor properties.

Aqueous-mediated N-alkylation of amines

Direct N-alkylation of primary amines to secondary/tertiary amines and of secondary amines to tertiary amines has been achieved in excellent yields by employing alkyl, benzylic and allylic halides in the presence of NaHCO 3 in an aqueous medium at an elevated temperature. Amines of different stereoelectronic nature react with ease with different halides. The selective formation of secondary amines and the formation of three different substituted tertiary amines are some of the interesting features of this methodology. Reaction in an aqueous medium, operationally convenient conditions, excellent yields and innocuous byproducts, and the absence of transition-metal catalysts, expensive bases, solid supports and the formation of undesired quaternary ammonium salts makes this method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.