Intramolecular Dehydrative Condensation of Dicarboxylic Acids with Brønsted Base-Assisted Boronic Acid Catalysts

• DOI: 10.1071/ch11301
• Publication Date: 2011-11-16T19:51:47Z
• Authors: Akira Sakakura; Risa Yamashita; Takuro Ohkubo; Matsujiro Akakura; Kazuaki Ishihara
• Keywords: Boronic acid; Brønsted–Lowry acid–base theory; Biocatalysis

Bifunctional Brønsted base-assisted boronic acid catalysts, arylboronic acids bearing two sterically bulky (N,N-dialkylamino)methyl groups at the 2,6-positions, exhibit remarkable activities for dehydrative intramolecular condensation of dicarboxylic acids. The steric bulkiness 1, which prevents formation less active species such as N→B chelated and triarylboroxines 3, is crucial high catalytic activity. This first successful method self-condensation di- tetracarboxylic