Sequential one-pot approach for the synthesis of functionalized phthalans via Heck-reduction–cyclization (HRC) reactions

Abstract

An efficient and practical method is described for the direct synthesis of 1,3-dihydroisobenzofurans, an important structural motif present in biologically active natural or synthetic compounds. The reaction was performed in an almost one-pot fashion via controlled [Pd]-catalyzed intermolecular Mizoroki–Heck coupling between 2-bromobenzaldehydes and allylic alcohols followed by reduction and treatment of crude diol with a Lewis acid to give 1,3-dihydroisobenzofurans. Significantly, the method enabled the synthesis of 1,3-dihydroisobenzofurans with simple to dense functionalities on the aromatic rings.