76691-55-9Relevant articles and documents
Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
Ramachandran, P. Veeraraghavan,Hamann, Henry J.
supporting information, p. 2938 - 2942 (2021/05/04)
Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.
Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids
Yildirim, Ayhan
, p. 947 - 951 (2015/08/06)
Abstract An efficient and inexpensive procedure for direct conversion of aliphatic carboxylic acids into amides has been developed using anilines or aliphatic amines and Mg(0) as catalyst in toluene. The amides were obtained by single crystallization in moderate to excellent yields with high purity. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis of medium and large cyclic amines in rhodium-catalysed reactions of aminoalkenes with H2/CO1
Bergmann, David J.,Campi, Eva M.,Roy Jackson,Patti, Antonio F.,Saylik, Dilek
, p. 835 - 844 (2007/10/03)
Rhodium-catalysed reactions of N-benzyl- or N-alkyl-aminoalkenes (6) with H2/CO can give cyclic amines (7) (7-13 ring size) in good to excellent yields when BIPHEPHOS is used as a ligand. Hydrogenation of the aminoalkene becomes a competing reaction for the smaller rings but can be overcome by using a H2/CO gas ratio of 1:5. Reactions of 2-alkenyloxybenzylamines (13) gave 9-, 12- and 17-membered rings (14) in 30-40% yield, but dimer formation (16) and/or hydrogenation were competing reactions. Similar reactions of alkenylamides and ortho-alkenylanilines gave only non-cyclized amino aldehydes as products in low isolated yields.