Exploiting the Hydrogen-Bonding Capacity of Organoboronic Acids to Direct Covalent Bond Formation in the Solid State: Templation and Catalysis of the [2 + 2] Photodimerization

Abstract

The ability of organoboronic acids to direct intermolecular [2 + 2] photodimerizations in the solid state is identified. The reactivity of 1,2-bis(4-pyridyl)ethylene (bpe) within cocrystals of discrete hydrogen-bonded molecular assemblies generates rctt-tetrakis(4-pyridyl)cyclobutane (tpcb) stereoselectively and in up to quantitative yield. Dry grinding of the boronic acids and excess bpe reveal the acids to function as supramolecular catalysts.