Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Akira Yoshimura; Kyle R. Middleton; Chenjie Zhu; Victor N. Nemykin; Viktor Zhdankin

doi:10.1002/anie.201203925

Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Akira Yoshimura, Kyle R. Middleton, Chenjie Zhu, Victor N. Nemykin, Viktor Zhdankin

Chemistry & Biochemistry

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64 Scopus citations

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 (US)
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
State	Published - Aug 6 2012

Keywords

aziridination
hypoiodous acid
iodine
organocatalysis
oxidation

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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).",

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AU - Zhdankin, Viktor

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KW - hypoiodous acid

KW - iodine

KW - organocatalysis

KW - oxidation

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Hypoiodite-mediated metal-free catalytic aziridination of alkenes

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