Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Abstract

Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).

Original language	English
Pages (from-to)	8059-8062
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	32
DOIs	https://doi.org/10.1002/anie.201203925
Publication status	Published - 6 Aug 2012
Externally published	Yes

Keywords

aziridination
hypoiodous acid
iodine
organocatalysis
oxidation

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201203925

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@article{294df72ba94a41c7a13203387dd170ec,

title = "Hypoiodite-mediated metal-free catalytic aziridination of alkenes",

abstract = "Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).",

keywords = "aziridination, hypoiodous acid, iodine, organocatalysis, oxidation",

author = "Akira Yoshimura and Middleton, {Kyle R.} and Chenjie Zhu and Nemykin, {Victor N.} and Zhdankin, {Viktor V.}",

year = "2012",

month = aug,

day = "6",

doi = "10.1002/anie.201203925",

language = "English",

volume = "51",

pages = "8059--8062",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "32",

}

TY - JOUR

T1 - Hypoiodite-mediated metal-free catalytic aziridination of alkenes

AU - Yoshimura, Akira

AU - Middleton, Kyle R.

AU - Zhu, Chenjie

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor V.

PY - 2012/8/6

Y1 - 2012/8/6

N2 - Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).

AB - Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).

KW - aziridination

KW - hypoiodous acid

KW - iodine

KW - organocatalysis

KW - oxidation

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DO - 10.1002/anie.201203925

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JO - Angewandte Chemie - International Edition

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