Trimethylamine-Borane as Useful Reagent in theN-Acylation orN-Alkylation of Amines by Carboxylic Acids

N‐Acylhydrazines: Future Perspectives Offered by New Syntheses and Chemistry

“…In addition, the chloroborane 17 is formed, and this is transformed into acyloxyborane 18 by treatment with the carboxylic acid R 3 COOH, added to the reaction mixture after the reduction step. The acyloxyborane 18 is known to be an acylating species [21,22] and therefore acylates the hydrazine to give the corresponding hydrazides 15. This ''one-pot, multi-step'' synthesis of hydrazides has a number of advantages: i) high hydrazide yields, ii) few by-products, iii) easy purification, iv) the use of solvent and reagents that are available in bulk and in principle compatible with an industrial process, and v) short reaction times.…”

Greener Synthesis of an Amide by Direct Reaction of an Acid and Amine under Catalytic Conditions

“…The resulting solid was dried (3.93-5.64 g, 62-89%), dissolved in CDCl 3 , and analyzed by NMR. No signals corresponding to protons of the starting materials were detected in this sample [16,17].…”

Symmetrical Tertiary Amines: Applications and Synthetic Approaches

“…In 1983 Trapani and coauthors reported the use of the trimethylamine-borane complex as a reducing agent for the N-alkylation of amines with carboxylic acids (Scheme 75). [193] This approach leads to Bn 3 N from Bn 2 NH or BnNH 2 in a moderate yield without the addition of any special catalysts or additives. In 2019 Adolfsson and co-authors have shown that molybdenum carbonyl can catalyze a similar reaction with silane as a reducing agent.…”