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

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

72 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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10.1002/anie.201203925

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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 Viktor Zhdankin",

year = "2012",

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doi = "10.1002/anie.201203925",

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journal = "Angewandte Chemie - International Edition",

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AU - Yoshimura, Akira

AU - Middleton, Kyle R.

AU - Zhu, Chenjie

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor

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

UR - https://www.scopus.com/pages/publications/84864751447

UR - https://www.scopus.com/pages/publications/84864751447#tab=citedBy

U2 - 10.1002/anie.201203925

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AN - SCOPUS:84864751447

SN - 1433-7851

VL - 51

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Abstract

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