Das, Kanu published the artcileN-Alkylation of Amines Catalyzed by a Ruthenium-Pincer Complex in the Presence of in situ Generated Sodium Alkoxide, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is secondary amine preparation density functional theory; alc primary amine alkylation ruthenium catalyst.
The use of ruthenium-NNN-pincer complexes of the type (R2NNN)RuCl2(PPh3) (R = tBu, iPr, Cy and Ph) for the catalytic N-alkylation of primary amines R-NH2 (R = Ph, propan-2-yl, thiophen-2-ylmethyl, etc.) under solvent-free conditions were reported. For the first time, the base that is required to promote these reactions is generated in situ from the alcs. R1-OH (R1 = Bu, (4-fluorophenyl)methyl, furan-2-ylmethyl, etc.) by the use of sodium. The resulting sodium alkoxide regenerates the alcs. substrate while acting as the water scavenger thus mitigating the need of an addnl. base. Among the catalysts screened, (tBu2NNN)RuCl2(PPh3) (0.02 mol-%) gives very high turnovers and good yields at 140 °C. The (tBu2NNN)RuCl2(PPh3) catalyzed N-alkylation tolerates a variety of amine and alc. substrates. While excellent turnover (29000) was obtained for the (tBu2NNN)RuCl2(PPh3) (0.002 mol-%) catalyzed alkylation of aniline with cyclohexyl methanol, the turnovers obtained in the corresponding catalytic methylation of p-anisidine was also very high (12000). The (tBu2NNN)RuCl2(PPh3) catalyzed reactions have also been accomplished under open-vessel conditions resulting in a net dehydrogenative coupling reaction. This protocol has been used to transform benzene-1,2-diamine to benzimidazoles I (R2 = H, F, OMe) with high productivity (12000 turnovers). DFT studies indicate that while β-hydride elimination is rate-determining (RDTS: 24.31 kcal/mol) for the alc. dehydrogenation segment which is endothermic, insertion of the imine is rate-determining (RDTS: 11.26 kcal/mol) for its hydrogenation that is exothermic.
European Journal of Organic Chemistry published new progress about Alkylation. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Recommanded Product: 4-Methoxy-N-methylaniline.
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem