Exploration of 1,2-phenylenediboronic esters as potential bidentate catalysts for organic synthesis
Recently, we described the first inverse electron demand Diels-Alder reaction of 1,2-diazene catalyzed by a bidentate Lewis acid. Herein we investigate 1,2-phenylenediboronic esters as potential catalysts for this transformation offering higher stability and easier handling than the currently used boranthracene derivatives. Different 1,2-phenylenediboronic esters were prepared and their ability to form bidentate coordination complexes with phthalazine was analyzed. Although a 1:1 complex was observed, X-ray analysis revealed binding only in a monodentate fashion.
Bader, Samuel L.,Kessler, Simon N.,Zampese, Jennifer A.,Wegner, Hermann A.