Synthesis of 2-hydroxy-3-substituted naphthoquinones using the Heck reaction

Abstract

An efficient Heck coupling of 2-hydroxy-3-iodo-naphthoquinone with a series of electron-deficient alkenes in aqueous solution has been accomplished. The method is characterized by simple conditions and facile work-up to isolate the products in good to excellent yields. The products contain the motif present in several naphthoquinone pigments but with enhanced polarity.