Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters

Abstract

A cyanoalkyl-hydroxylation reaction of aryl alkenes has been successfully devised, employing ferrocene as a catalyst for the addition of a cycloketone oxime ester and H₂O across the double bond of the alkene. This environmentally friendly approach employs a solvent mixture consisting of water and demonstrates redox neutrality, along with exceptional regio- and chemoselectivity, leading to the formation of diverse distal hydroxy-nitrile compounds. Moreover, this research presents noteworthy contributions in terms of late-stage functionalization of complex molecules and offers valuable insights into the mechanistic aspects of the reaction.