6290-46-6Relevant academic research and scientific papers
A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids
Pathak, Gunindra,Das, Diparjun,Rokhum, Lalthazuala
, p. 93729 - 93740 (2016/10/21)
The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic route is incorporated for the said conversion, which has added advantages over solution-phase pathways, such as low moisture sensitivity, easy handling, isolation of the product by simple filtration, and reusability. In short, our method is simple, mild, green, and highly chemoselective in nature.
Primary alkylboronic acids as highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids
Yamashita, Risa,Sakakura, Akira,Ishihara, Kazuaki
, p. 3654 - 3657 (2013/08/23)
Primary alkylboronic acids such as methylboronic acid and butylboronic acid are highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids. The catalytic activities of these primary alkylboronic acids are much higher than those of the previously reported arylboronic acids. The present method was easily applied to a large-scale synthesis, and 14 g of an amide was obtained in a single reaction.
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.
N-alkyl-4-boronopyridinium halides versus boric acid as catalysts for the esterification of α-hydroxycarboxylic acids
Maki, Toshikatsu,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 5047 - 5050 (2007/10/03)
(Chemical Equation Presented) Boric acid is a highly effective catalyst for the dehydrative esterification reaction between equimolar mixtures of α-hydroxycarboxylic acids and alcohols. In contrast, N-methyl-4- boronopyridinium iodide (2a) is a more effective catalyst than boric acid for the similar esterification in excess alcohol. A heterogeneous catalyst, such as N-polystyrene-bound 4-boronopyridinium chloride, is also an effective catalyst and can be recovered by filtration.
An efficient and convenient procedure for preparation of mandelates catalysed by TiO2/SO4/2- solid superacid
Jin,Ma,Li,Sun,Li
, p. 2051 - 2054 (2007/10/03)
An easy and efficient synthesis of mandelates in excellent yields from mandelic acid with alcohols catalysed by TiO2/SO42- solid superacid.
Fe2(SO4)3 · xH2O in synthesis: A new and convenient catalyst for the esterification of mandelic acid with alcohols
Zhang, Gui-Sheng,Gong, Hui
, p. 1547 - 1551 (2007/10/03)
Treatment of various of alcohols with mandelic acid in the presence of a catalytic amount of Fe2(SO4)3 · xH2O to give the corresponding esters in good yields.
A general and simple synthesis of phenylglyoxylic esters via the oxidation of mandelic esters with ammonium chlorochromate adsorbed on alumina
Zhang, Gui-Sheng,Gong, Hui
, p. 3149 - 3153 (2007/10/03)
A general method for preparation of phenylglyoxylic esters by oxidation of mandelic esters with readily available ammonium chlorochromate adsorbed on alumina is described.
