Synthesis and structure of potential Lewis acid–Lewis base bifunctional catalysts: 1-N,N-dimethylamino-8-borononaphthalene derivatives

A new series of boronate-amine substituted potential bifunctional catalysts have been prepared by directed lithiation of 1-N,N-dimethylnaphthalene, followed by reaction borate esters. Both diisopropyl and pincacol ester derivatives of the resulting boronates were prepared, together with a novel boroxine which shows novel N–B interactions in the crystal structure. The corresponding dimethyl-[8-(difluoroborolyl)-naphthalen-1-yl]-amine was directly accessed from the boroxine by reaction with potassium hydrogen fluoride.