Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes.

ABSTRACT: Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional

SUBMITTER: Bhunia A 

PROVIDER: S-EPMC8049001 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature