33282-15-4, Name is 5-(4-Hydroxyphenyl)isoxazole-3-carboxylic acid, belongs to isoxazole compound, is a common compound. Application In Synthesis of 5-(4-Hydroxyphenyl)isoxazole-3-carboxylic acidIn an article, once mentioned the new application about 33282-15-4.
An efficient method for the synthesis of tertiary amines through a gold(I)-catalyzed tandem reaction of alkynes with secondary amines has been developed. In the presence of ethyl Hantzsch ester and [{(tBu) 2(o-biphenyl)P}AuCl]/AgBF4 (2 mol %), a variety of secondary amines bearing electron-deficient and electron-rich substituents and a wide range of alkynes, including terminal and internal aryl alkynes, aliphatic alkynes, and electron-deficient alkynes, underwent a tandem reaction to afford the corresponding tertiary amines in up to 99 % yield. For indolines bearing a preexisting chiral center, their reactions with alkynes in the presence of ethyl Hantzsch ester catalyzed by [{(tBu)2(o-biphenyl)P}AuCl]/AgBF 4 (2 mol %) afforded tertiary amines in excellent yields and with good to excellent diastereoselectivity. All of these organic transformations can be conducted as a one-pot reaction from simple and readily available starting materials without the need of isolation of air/moisture-sensitive enamine intermediates, and under mild reaction conditions (mostly room temperature and mild reducing agents). Mechanistic studies by NMR spectroscopy, ESI-MS, isotope labeling studies, and DFT calculations on this gold(I)-catalyzed tandem reaction reveal that the first step involving a monomeric cationic gold(I)-alkyne intermediate is more likely than a gold(I)-amine intermediate, a three-coordinate gold(I) intermediate, or a dinuclear gold(I)-alkyne intermediate. These studies also support the proposed reaction pathway, which involves a gold(I)-coordinated enamine complex as a key intermediate for the subsequent transfer hydrogenation with a hydride source, and reveal the intrinsic stereospecific nature of these transformations observed in the experiments. Producing tertiary amines: The AuI-catalyzed tandem reaction of alkynes with secondary amines provides simple and efficient access to highly substituted tertiary amines with excellent yields and good to excellent diastereoselectivity. Mechanistic studies confirm that a possible reaction pathway involves intermolecular hydroamination via a monomeric cationic gold(I)-alkyne intermediate and subsequent transfer hydrogenation via a gold(I)-coordinated enamine intermediate. Copyright
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem