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

Alexandra M. Millimaci; Rowan I.L. Meador; Sara J. Dampf; John D. Chisholm

doi:10.1002/ijch.202000080

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

Alexandra M. Millimaci, Rowan I.L. Meador, Sara J. Dampf, John D. Chisholm

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	322-326
Number of pages	5
Journal	Israel Journal of Chemistry
Volume	61
Issue number	5-6
DOIs	https://doi.org/10.1002/ijch.202000080
State	Published - May 2021

Keywords

alkenes
amination
oxidation
oxoammonium
regioselective

ASJC Scopus subject areas

General Chemistry

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10.1002/ijch.202000080

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title = "Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt",

abstract = "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.",

keywords = "alkenes, amination, oxidation, oxoammonium, regioselective",

author = "Millimaci, {Alexandra M.} and Meador, {Rowan I.L.} and Dampf, {Sara J.} and Chisholm, {John D.}",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH.",

year = "2021",

month = may,

doi = "10.1002/ijch.202000080",

language = "English (US)",

volume = "61",

pages = "322--326",

journal = "Israel Journal of Chemistry",

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TY - JOUR

T1 - Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

AU - Millimaci, Alexandra M.

AU - Meador, Rowan I.L.

AU - Dampf, Sara J.

AU - Chisholm, John D.

PY - 2021/5

Y1 - 2021/5

N2 - 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.

AB - 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.

KW - alkenes

KW - amination

KW - oxidation

KW - oxoammonium

KW - regioselective

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DO - 10.1002/ijch.202000080

M3 - Article

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VL - 61

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EP - 326

JO - Israel Journal of Chemistry

JF - Israel Journal of Chemistry

IS - 5-6

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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