Studies on the alkylation of phenolate in an organofluorine solvent and its application to the synthesis of myrsinoic acids A and E

Article abstract of DOI:10.1080/00397911.2017.1288823

Among the distinct features of organofluorines, solubility properties to molecules often enable unique applications. More importantly, organofluorines can be compatible with chemical reactions in general, even under harsh conditions. In this context, a study on the alkylation of phenolate using an organofluorine solvent were performed for the preparation of ortho-alkyl phenols. Herewith, the study on the alkylation of phenolate in an organofluorine solvent as well as its application to the synthesis of bioactive terpenylated phenolic natural products, myrsinoic acids A and E, will be reported. Our study suggested that organofluorine solvents could be better alternatives to the conventional nondissociating solvents as organic reaction media to suppress the nondesirable and nonselective side reactions such as in the ortho-alkylation of phenolate.