Unsaturated phosphonates as Hauser Acceptors for the synthesis of phosphonylated dihydroxy naphthalenes and naphthoquinones

Abstract

The unsaturated phosphonates were utilized as Hauser acceptors successfully for the first time. The products phosphonylated 1,4-dihydroxynaphthalenes were isolated in good yields in short reaction time and were further oxidized to the corresponding 1,4-naphthoquinones in quantitative yields. The reaction provides an efficient and straightforward approach for the synthesis of pharmacologically privileged disubstituted naphthalene-1,4-diols and naphtha-1,4-diones bearing phosphonate group at 2- and various (het)aryl groups at 3-position.