Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile

Akira Yoshimura, T. Nicholas Jones, Mekhman S. Yusubov, Viktor Vladimirovich Zhdankin

Research School of Chemistry & Applied Biomedical Sciences

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

Abstract

An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.

Original language	English
Pages (from-to)	3336-3340
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	16
DOIs	https://doi.org/10.1002/adsc.201400627
Publication status	Published - 21 Sep 2014

Keywords

Cyclopropanation
Hypoiodite
Iodine
Organocatalysis
Oxidation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201400627

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title = "Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile",

abstract = "An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.",

keywords = "Cyclopropanation, Hypoiodite, Iodine, Organocatalysis, Oxidation",

author = "Akira Yoshimura and {Nicholas Jones}, T. and Yusubov, {Mekhman S.} and Zhdankin, {Viktor Vladimirovich}",

year = "2014",

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doi = "10.1002/adsc.201400627",

language = "English",

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T1 - Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile

AU - Yoshimura, Akira

AU - Nicholas Jones, T.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor Vladimirovich

PY - 2014/9/21

Y1 - 2014/9/21

N2 - An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.

AB - An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.

KW - Cyclopropanation

KW - Hypoiodite

KW - Iodine

KW - Organocatalysis

KW - Oxidation

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DO - 10.1002/adsc.201400627

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EP - 3340

JO - Journal fur Praktische Chemie

JF - Journal fur Praktische Chemie

SN - 1436-9966

IS - 16