Metal Free Amino‐Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

4‐Acetamido‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate (Bobbitt's salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino‐oxidation of alkenes under mild conditions. The r...

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Bibliographic Details
Published in:Israel journal of chemistry 2021-05, Vol.61 (5-6), p.322-326
Main Authors: Millimaci, Alexandra M., Meador, Rowan I. L., Dampf, Sara J., Chisholm, John D.
Format: Article
Language:English
Subjects:
Alkenes
amination
Aniline
Oxidation
oxoammonium
regioselective
Solvent effect
Stereochemistry
Transition metals
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Summary:4‐Acetamido‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate (Bobbitt's salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino‐oxidation of alkenes under mild conditions. The relative stereochemistry of the amino‐oxidation is influenced by solvent effects, with both the syn and anti amino‐oxidation products being accessible from identical starting materials.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.202000080