Synthesis of 1,2,4,5-oxadiazaboroles by three-component condensations of hydroxylamines, nitriles, and diarylborinic acids

A method for the synthesis of substituted 1,2,4,5-oxadiazaboroles is described, in which hydroxylamines, nitriles, and diarylborinic acids engage in a three-component condensation reaction. The protocol provides access to a substitution pattern that is not readily available through other methods--namely, 2,3-disubstitution, with a tetracoordinate boron center. Structures of representative members of this class of heterocycles were determined by single crystal X-ray diffraction analysis. Key words: boron, condensation, heterocycles, nitriles
Introduction Boron-based heterocycles are of interest from several perspectives, (1) including fundamental studies of structure, bonding, reactivity, and photophysical properties, along with potential applications in material science, (2) catalysis, (3) [...]