Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis
نویسندگان
چکیده
منابع مشابه
Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines.
Arylboronic acids were found to be efficient catalysts for the amidation reactions between carboxylic acids and amines. Theoretical calculations have been carried out to investigate the mechanism of this catalytic process. It is found that the formation of the acyloxyboronic acid intermediates from the carboxylic acid and the arylboronic acid is kinetically facile but thermodynamically unfavora...
متن کاملRu-catalyzed 1,4-addition of arylboronic acids to acrylic acid derivatives in the presence of phenols.
[Ru(p-cymene)Cl2]2-catalyzed 1,4-addition reactions between arylboronic acids and butyl acrylate and acrylamide in the presence of phenols were investigated, good to excellent yields were obtained. The addition of phenols remarkably promoted the protonolysis and inhibited the β-H elimination of the 1,4-addition intermediates, and also efficiently suppressed the protonolysis of arylboronic acids.
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A series of arylidine barbituric acid derivatives was synthesized by Knoevenagel condensation reaction of aromatic aldehydes with barbituric acid or thiobarbituric acid using dodecylbenzenesulfonic acid as a Brønsted acid-surfactant catalyst in aqueous media. Regardless of the nature of the substitution (electron-donating and -withdrawing), all the reactions were completed within 15-65 min in w...
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A series of arylidine barbituric acid derivatives was synthesized by Knoevenagel condensation reaction of aromatic aldehydes with barbituric acid or thiobarbituric acid using dodecylbenzenesulfonic acid as a Brønsted acid-surfactant catalyst in aqueous media. Regardless of the nature of the substitution (electron-donating and -withdrawing), all the reactions were completed within 15-65 min in w...
متن کاملPalladium(III)-catalyzed fluorination of arylboronic acid derivatives.
A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.
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ژورنال
عنوان ژورنال: European Journal of Organic Chemistry
سال: 2013
ISSN: 1434-193X
DOI: 10.1002/ejoc.201300560