Advances in the Ring Opening of Small-Ring Heterocycles with Organoboron Derivatives

This is a personal account on how our research group has exploited trivalent boron-containing organic compounds to create new synthetic methods using small-ring heterocycles. A variety of new regioselective ring-opening reactions (including phenolysis and arylation) that exhibit unusual syn-stereoselectivities can be achieved by making use of the Lewis acidity of boron in aryloxyboranes. On the other hand, the use of the nucleophilic character of diboron derivatives permits regio- and stereocontrolled formation of new C-B bonds. An up-to-date critical coverage of recent relevant literature in the field is also provided.