Manganese-catalyzed aziridination of olefins with chloramine-T in water and buffered aqueous solutions

A water-soluble, manganese-porphyrin complex was used to catalytically generate aziridines from olefins in moderate to good yields (up to 93%) upon optimization at room temperature and in aqueous media. Reactions using chloramine-T at slightly acidic to neutral pH values showed generally higher cata...

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Bibliographic Details
Published inCatalysis communications Vol. 150; p. 106275
Main Authors Wolgemuth, Daniel K., Elmore, Sydnee D., Cope, James D., Sheridan, Patrick E., Stokes, Sean L., Emerson, Joseph P.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.02.2021
Elsevier
Subjects
Aziridination
Catalysis
Chloramine-T
Manganese
Nitrene transfer
TMPyP4
Catalysis
Nitrene transfer
TMPyP4
Aziridination
Chloramine-T
Manganese
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Summary:A water-soluble, manganese-porphyrin complex was used to catalytically generate aziridines from olefins in moderate to good yields (up to 93%) upon optimization at room temperature and in aqueous media. Reactions using chloramine-T at slightly acidic to neutral pH values showed generally higher catalytic yields. Attempts to integrate this catalytic system into a DNA hybrid catalyst system to support asymmetric aziridination showed little promise, where steric bulk in the axial positions from activation of chloramine-T by this Mn-heme complex may influence its ability to associate with double-stranded DNA. [Display omitted] •Mn-TMPyP4 can utilize chloramine-T as an effective nitrene source to produce aziridines in water and buffered aqueous media.•[Mn(TMPyP4)]I5 complex was used as the catalyst for aziridination with moderate to good yields with a range of olefins.•Addition of several different DNA samples as a chiral auxiliary did not result in enantioselective aziridination.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2020.106275