Transition metal catalyzed carboannulation of diazabicyclic alkenes with ambiphilic bifunctional reagents: A facile route towards functionalized indanones and indanols

Abstract

Functionalized indanones are readily prepared in good to excellent yields by the Pd/Rh catalyzed carboannulation of bicyclic and tricyclic hydrazines with 2-iodobenzonitrile, 2-cyanophenylboronic acid and 2-formylphenylboronic acid. The reaction with 2-formylphenylboronic acid afforded 3,4-disubstituted cyclopentenes as minor product along with indanones under Rh catalyzed conditions, whereas indanols were obtained as the major product under Pd catalyzed conditions. The products obtained can be synthetically manipulated easily to pharmaceutically important molecules.