Various Synthetic Methods Using Aromatic Carboxylic Anhydrides

Abstract

As a result of pursuing dehydrating condensation reagents, which can be stably stored at room temperatures, easy to handle, and highly reactive, it was found that aromatic carboxylic anhydrides can be used as versatilely highly functional reagents. Reaction by using TFBA or BTFBA with a Lewis acid catalyst can be one of the most powerful protocols for carbon-oxygen bond formation, which enable the synthesis of the desired carboxylic esters and lactones in good yields. Furthermore, the use of MNBA or DMNBA with a nucleophilic catalyst under basic conditions enables convenient preparation of acid- sensitive carboxylic esters, lactones, and amides. In addition, the use of PMBA or benzoic anhydride with an asymmetric catalyst realizes the kinetic resolution of racemic secondary alcohols and racemic 2-arylpropionic acids, resulting in the establishment of a novel synthetic method for optically active carboxylic esters, secondary alcohols, and 2-arylpropionic acids.