Synthesis of 2,2′‐Biflavanones from Flavone via Electrolytic Reductive Coupling

Flavone ( 1 ) was easily reduced by using the electrochemical method to give two hydrodimers of 2,2′‐biflavanone(racemate) ( 5a ) and 2,2′‐biflavanone(meso) ( 5b ) and one reductive product of flavanone ( 6 ). Their yields were dependent on the nature of electrodes, the kinds of supporting electrolytes and the reaction temperature. They were found to afford higher yields of 2,2′‐biflavanone(racemate) ( 5a ) and 2,2′‐biflavanone (meso) ( 5b ) (32.4% and 24.8%, 35.8% and 13.4%, respectively,) in the reaction conditions of Pb(‐)/C(+)‐H₂SO₄‐7F/mol and C(‐)/C(+)‐H₂SO₄‐5F/mol.