Hypoiodite‐Mediated Metal‐Free Catalytic Aziridination of Alkenes

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 o...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-08, Vol.51 (32), p.8059-8062
Main Authors: Yoshimura, Akira, Middleton, Kyle R., Zhu, Chenjie, Nemykin, Victor N., Zhdankin, Viktor V.
Format: Article
Language:English
Subjects:
Alkenes
aziridination
Catalysis
Catalysts
hypoiodous acid
Iodides
iodine
organocatalysis
Oxidants
oxidation
Oxidizing agents
Precursors
Terminals
X-rays
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Summary: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203925