Electrochemically Enabled Carbohydroxylation of Alkenes with H₂O and Organotrifluoroborates

Abstract

Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H₂O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electrochemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.