CBr4 promoted intramolecular aerobic oxidative dehydrogenative arylation of aldehydes: application in the synthesis of xanthones and fluorenones

Abstract

A simple and practical carbon tetrabromide promoted intramolecular aerobic oxidative dehydrogenative coupling reaction has been developed to provide a straightforward ring closure protocol for 2-aryloxybenzaldehydes to furnish xanthones. The reaction was performed under metal-, additive- and solvent-free conditions with good tolerance of functional groups. The present method is also applicable to the synthesis of fluorenones by using 2-arylbenzaldehydes as substrates. Preliminary studies of the reaction mechanism indicated that the reaction may proceed through a radical pathway.