Catalytic reductive N-alkylation of amines using carboxylic acids.

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.

A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three com...

Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines.

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reduc...

Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines

Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from...

Selective reductive amination of aldehydes from nitro compounds catalyzed by molybdenum sulfide clusters†

Amines are the most important building blocks employed in modern medicinal chemistry. Secondary amines are regularly prepared by the alkylation or reductive amination of the parent amines through transition metal, typically precious metals, catalyzed reactions. In the past few years, the catalytic alkylation of amines with alcohols under hydrogenborrowing conditions as well as the catalytic red...

Cobalt-catalysed reductive C–H alkylation of indoles using carboxylic acids and molecular hydrogen† †Electronic supplementary information (ESI) available: General information concerning experimental procedures, additional tables, figures, schemes, characterization data and NMR spectra of the isolated compounds are available. See DOI: 10.1039/c7sc02117h