Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters.

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.

Divergent cyanoalkylation/cyanoalkylsulfonylation of enamides under organophotoredox catalytic conditions.

An organophotoredox-catalyzed divergent cyanoalkylation/cyanoalkylsulfonylation of enamides in a highly regio- and stereoselective manner has been reported. In this mild and efficient protocol, cyclobutanone oxime esters serve as a cyanoalkylating source and inexpensive K2S2O5 serves as an SO2 surrogate. Broad substrate scope, compatibility of various sensitive functional groups and further functional group transformation are the highlights of this method.

Organophotoredox-catalyzed cyanoalkylation of 1,4-quinones.

A visible-light-induced metal-free cyanoalkylation of 1,4-quinones under mild and redox-neutral conditions is described. This reaction proceeds at room temperature without the need of extra base or additive and is suitable for a variety of 1,4-quinones and differently substituted cyclobutanone oxime esters. Further transformation of cyano functionality to tetrazole and amine has also been demonstrated to showcase the advantage of this method to prepare drug-like molecules.

Ferrocene catalyzed redox-neutral difunctionalization of alkenes using cycloketone oxime esters: access to distal imido-nitriles.

A novel ferrocene-catalyzed cyanoalkyl-imidation of aryl alkenes utilizing cycloketone oxime esters in MeCN under redox-neutral conditions is described. In this three-component reaction, the cycloketone oxime ester is employed as a bifunctional reagent, enabling easy access to diverse distal imido-nitriles with 100% atomic utilization. Preliminary mechanistic studies suggest that the ferrocene-ferrocenium catalytic cycle is responsible for the deconstructive functionalization of cycloketone oxime esters.