Electrochemical ring-opening 1,3-dihydroxylation of arylcyclopropanes with H2O

Abstract

Conventional dihydroxylation of alkenes is one of the most powerful synthetic tools for delivering two hydroxyl groups at vicinal positions. The direct formation of 1,3-diols remains a formidable challenge, yet dihydroxyl groups are broadly present in bioactive compounds, and are currently only available synthetically via multiple steps. The oxidative ring-opening of arylcyclopropanes has been demonstrated to access various 1,3-difunctionalized chemicals, but no 1,3-diols have been directly synthesized owing to their inherently high proclivity to become further oxidized. Herein, we report a facile and efficient strategy to 1,3-diols involving controlled electrochemical C–C bond cleavage of arylcyclopropanes with H₂O as the ultimately green hydroxyl source. Moreover, this protocol stands out with its high atom economy, broad substrate scope and excellent functional group tolerance, and hence is amenable to the synthesis of complex natural products and drug derivatives.