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Fe‐Catalyzed Anaerobic Mukaiyama‐Type Hydration of Alkenes using Nitroarenes
Author(s) -
Bhunia Anup,
Bergander Klaus,
Daniliuc Constantin Gabriel,
Studer Armido
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202015740
Subject(s) - alkene , chemistry , markovnikov's rule , nitro , catalysis , moiety , selectivity , reagent , surface modification , combinatorial chemistry , functional group , stereoselectivity , oxygen , organic chemistry , regioselectivity , alkyl , polymer
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 for late‐stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.