O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates

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Abstract

Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic solvents and are efficient reagents for the catalytic aziridination of alkenes or the metal-free tosylamination of organic substrates (see scheme, Ts=tosyl).

Original languageEnglish
Pages (from-to)10538-10541
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number38
DOIs
Publication statusPublished - 12 Sep 2011
Externally publishedYes

Fingerprint

Amination
Alkenes
Organic solvents
Olefins
Solubility
Metals
Substrates
phenylnitrene

Keywords

  • amination
  • aziridination
  • hypervalent compounds
  • iodine
  • oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates",
abstract = "Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic solvents and are efficient reagents for the catalytic aziridination of alkenes or the metal-free tosylamination of organic substrates (see scheme, Ts=tosyl).",
keywords = "amination, aziridination, hypervalent compounds, iodine, oxidation",
author = "Akira Yoshimura and Nemykin, {Victor N.} and Zhdankin, {Viktor V.}",
year = "2011",
month = "9",
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doi = "10.1002/chem.201102265",
language = "English",
volume = "17",
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journal = "Chemistry - A European Journal",
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publisher = "Wiley-VCH Verlag",
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TY - JOUR

T1 - O-alkoxyphenyliminoiodanes

T2 - Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates

AU - Yoshimura, Akira

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor V.

PY - 2011/9/12

Y1 - 2011/9/12

N2 - Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic solvents and are efficient reagents for the catalytic aziridination of alkenes or the metal-free tosylamination of organic substrates (see scheme, Ts=tosyl).

AB - Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic solvents and are efficient reagents for the catalytic aziridination of alkenes or the metal-free tosylamination of organic substrates (see scheme, Ts=tosyl).

KW - amination

KW - aziridination

KW - hypervalent compounds

KW - iodine

KW - oxidation

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DO - 10.1002/chem.201102265

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JO - Chemistry - A European Journal

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SN - 0947-6539

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