Fe-catalyzed anaerobic Mukaiyama-type hydration of alkenes using nitroarenes.

Fe-catalyzed anaerobic Mukaiyama-type hydration of alkenes using nitroarenes.
Angew Chem Int Ed Engl. 2021 Jan 21;:
Authors: Bhunia A, Bergander K, Daniliuc CG, Studer A
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 group tolerance and is also applicable to highly diastereoselective alkene hydration of natural products, qualifying the protocol for late-stage chemical functionalization. It is shown that the anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
PMID: 33476093 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 21, 2021 Category: Chemistry Authors: Bhunia A, Bergander K, Daniliuc CG, Studer A Tags: Angew Chem Int Ed Engl Source Type: research