Studies On The Transition Metal-Catalyzed Esterification And Methylthiolation

The reactions of esterification and methylthiolation play important roles in organic chemistry. As we know, the transition-metal-catalyzed reactions are simple, efficient and versatile routes to the formation of C-C and C-S bonds.This dissertation consisted of two parts. The first one is focused on the transition metal-catalyzed esterification. The second one is focused on copper-mediated methylthiolation of aryl halides. In part one, the recent research progress on esterification was simply reviewed and four novel reactions were studied as follows: (1) a copper-catalyzed esterification reaction of arene carboxylic acids with aryl trimethoxysilanes was described. Notably, it also represents a facile and versatile method to access vinyl benzoate derivatives; (2) a copper-catalyzed esterification reaction of dicarboxylic internal anhydride with aryl and vinyl alkoxysilanes is described, in which the alkoxy and aryl (or vinyl) esters of dicarboxylic acids were prepared in one-pot with moderate to good yields; (3) a palladium/NHC-catalyzed tandem oxidation/esterification of benzylic alcohols with phenols to access aryl benzoate derivatives is described. (4) an efficient rhodium or palladium-catalyzed lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides has been developed, which represents a facile and practical methodology.In part two, the dissertation described that copper-mediated methylthiolation of ayl halides, using common solvent DMSO as the terminal methylthiolation source. The procedure tolerates a series of functional groups and proceeds smoothly with good yields.