Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Akira Yoshimura; Kyle R. Middleton; Anthony D. Todora; Brent J. Kastern; Steven R. Koski; Andrey V. Maskaev; Viktor Zhdankin

doi:10.1021/ol401815n

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Akira Yoshimura, Kyle R. Middleton, Anthony D. Todora, Brent J. Kastern, Steven R. Koski, Andrey V. Maskaev, Viktor Zhdankin

Chemistry & Biochemistry

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

148 Scopus citations

Abstract

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

Original language	English (US)
Pages (from-to)	4010-4013
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	15
DOIs	https://doi.org/10.1021/ol401815n
State	Published - Aug 2 2013

Access

10.1021/ol401815n

OpenUrl availability

Full text

Cite this

@article{57b39b1b819e47c1a0951614bd944315,

title = "Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes",

abstract = "Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.",

author = "Akira Yoshimura and Middleton, {Kyle R.} and Todora, {Anthony D.} and Kastern, {Brent J.} and Koski, {Steven R.} and Maskaev, {Andrey V.} and Viktor Zhdankin",

year = "2013",

month = aug,

day = "2",

doi = "10.1021/ol401815n",

language = "English (US)",

volume = "15",

pages = "4010--4013",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

AU - Yoshimura, Akira

AU - Middleton, Kyle R.

AU - Todora, Anthony D.

AU - Kastern, Brent J.

AU - Koski, Steven R.

AU - Maskaev, Andrey V.

AU - Zhdankin, Viktor

PY - 2013/8/2

Y1 - 2013/8/2

N2 - Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

AB - Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

UR - http://www.scopus.com/inward/record.url?scp=84881231428&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84881231428&partnerID=8YFLogxK

U2 - 10.1021/ol401815n

DO - 10.1021/ol401815n

M3 - Article

C2 - 23865434

AN - SCOPUS:84881231428

SN - 1523-7060

VL - 15

SP - 4010

EP - 4013

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Abstract

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this