Phosphonation of 1,1′-binaphthalene-2,2′-diol (BINOL): synthesis of (R)- and (S)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-diyldiphosphonic acid

Abstract

The synthesis of 6,6′-bis(diethoxyphosphoryl)-1,1′-binaphthalene-2,2′-diol 1 in racemic and chiral forms is described. This synthesis, which involves a palladium-assisted phosphonation step, allows study of the phosphonation of bromophenol as an electron-rich aryl bromide model. Furthermore, the synthesis of 2,2′-dihydroxy-1,1′-binaphthalene-6,6′-diyldiphosphonic acid 2, from its diester 1, leads to a key intermediate in the synthesis of hybrid organic-inorganic materials.