22635-28-5Relevant academic research and scientific papers
New boron(III)-catalyzed amide and ester condensation reactions
Maki, Toshikatsu,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 8645 - 8657 (2008/02/08)
In 1996, we reported that benzeneboronic acids bearing electron-withdrawing groups at the meta- or para-position are highly effective catalysts for the amide condensation reaction in less-polar solvents. In this paper, we report that N-alkyl-4-boronopyridinium halides are more effective catalysts than the previous ones in more polar solvents. N-Alkyl-4-boronopyridinium halides are effective not only for amide condensation between equimolar mixtures of carboxylic acids and amines but also for the esterification of α-hydroxycarboxylic acids in alcohol solvents. Furthermore, perchlorocatecholborane is more effective than areneboronic acids for the amide condensation of sterically demanding carboxylic acids. In addition, Lewis acid-assisted Br?nsted acid (LBA), which is prepared from a 1:2 M mixture of boric acid and tetrachlorocatechol, is effective for the Ritter reaction from alcohols and nitriles to amides.
4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids
Maki, Toshikatsu,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 1431 - 1434 (2007/10/03)
4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborole (4a) and 4,5,6,7- tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol (4b) are effective catalysts for the dehydrative amide condensation between an equimolar mixture of carboxylic acids and amines. In particular, these catalysts are greatly superior to 3,5-bis(trifluoromethyl)phenylboronic acid (1) for the amide condensation of sterically demanding carboxylic acids. In contrast, 4c, which is prepared from a 1:2 molar mixture of B(OH)3 and tetrachlorocatechol, is effective as a Lewis acid-assisted Bronsted acid (LBA) catalyst for Ritter reaction.
