Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Sulfoxonium Ylides for the Synthesis of α-Acetoxyl Ketones.

ABSTRACT

The most convenient and direct method of synthesizing an α-acyloxy ketone is the reaction of a diazo compound with a carboxylic acid via O-H insertion. However, due to the limitations in preparing and storing diazo compounds, the application of this method is restricted. In this study, Cu(OAc)2-mediated (OAc = acetate) decarboxylative coupling reactions of 3-indoleacetic acids with sulfoxonium ylides were developed for use in rapidly synthesizing α-acetoxyl ketones. In this reaction, Cu(OAc)2 was not only used as an oxidant, but also as acetate ion source. Notably, when 5-methoxy-2-methyl-3-indoleacetic acid reacted with different sulfoxonium ylides, the corresponding products exhibited fluorescence, and furthermore, several products displayed antiproliferative activities against various human cancer cell lines.