Development and Evaluation of Recyclable Catalystsfor Amide Bond Formation

• Main Authors: Ya-Ping Wen, 温雅評
• Other Authors: Lee-Chiang Lo
• Format: Others
• Language: en_US
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/cpg68z

碩士 === 國立臺灣大學 === 化學研究所 === 105 === Amide bond formation has been one of the most important reactions in organic synthesis. From natural biomolecules to synthetic products, the importance and utility of amide bonds have received tremendous attention for centuries. However, current synthetic strategies for amide bond formations still suffer from several drawbacks including the use of stoichiometric amounts of expensive coupling reagents as well as massive production of byproducts and wastes. Thus, there is a need for development of mild, simple and waste-free synthetic methods for amide bond formation. In this research, several phenylboronic acids capable of catalyzing direct amidation condensation between a carboxylic acid and an amine were designed and synthesized. These catalysts are found to be stable and functional under practical conditions, and can be recycled with more than 90% recovery. A series of amidation screening experiments were performed to assess the catalytic performance of these catalysts using a variety of carboxylic acid and amine substrates. Therefore, we believe that direct amidation reaction catalyzed by a recyclable boronic acid would be a promising synthetic method in the near future due to its efficiency, convenience, and most importantly, environmental friendly processes.