Study on the Regioselectivity of Rhodium-Catalyzed Ring Opening Reactions of C₁-Substituted 7-Oxabenzonorbornadienes with Boronic Acids

Abstract

An optimized condition for the rhodium-catalyzed ring-opening reaction of C₁-substituted oxabicyclic alkenes with aryl boronic acids was developed and the effect of aryl boronic acid as well as the effect of C₁ substitution on the oxabicyclic alkenes was studied. Aryl boronic acids carrying electron-donating substituents provided the ring-opened products in excellent yields regardless of the position, while electron-withdrawing substituents were more susceptible to steric interactions. Although two different regioisomers are possible, all the rhodium-catalyzed ring-opening reactions of C₁ substituted oxabicyclic alkenes studied with aryl boronic acids were found to be highly regioselective, giving single regioisomers in all cases.

GRAPHICAL ABSTRACT

Keywords:

• Boronic acids
• 7-oxabenzonorbornadienes
• regioselectivity
• rhodium catalysis
• ring-opening reactions