Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions

Jun Hee In; Se Eun Park; Rita Song; Wonwoo Nam

doi:10.1016/S0020-1693(02)01239-2

Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions

Jun Hee In, Se Eun Park, Rita Song, Wonwoo Nam

Department of Chemistry & Nanoscience

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

70 Scopus citations

Abstract

An electron-deficient iron(III) porphyrin complex associated with iodobenzene diacetate (PhI(OAc)₂) afforded high yields of oxygenated products in catalytic oxygenations of olefins and alkanes when the reactions were carried out in the presence of a small amount of water. An oxoiron(IV) porphyrin cation radical intermediate was generated in the reaction of an iron(III) porphyrin complex and PhI(OAc)₂. These results demonstrate that PhI(OAc)₂, which is soluble in organic media, safe to use, and readily available, is an efficient oxygen atom donor that can be used as a substitute for polymeric iodosylbenzene (PhIO) in metalloporphyrin-mediated oxygenation reactions.

Original language	English
Pages (from-to)	373-376
Number of pages	4
Journal	Inorganica Chimica Acta
Volume	343
DOIs	https://doi.org/10.1016/S0020-1693(02)01239-2
State	Published - 30 Jan 2003

Bibliographical note

Funding Information:
This research was supported by the Korea Science and Engineering Foundation (R03-2001-00028 to W.N. and R05-2000-0008 to R.S.), the Korea Research Foundation (DP0270), and Ewha Womans University (2000).

Keywords

Epoxidation
Hydroxylation
Iodobenzene diacetate
Iodosylbenzene
Iron(III) porphyrin

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10.1016/S0020-1693(02)01239-2

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@article{5f76e4be8834478fb22d7ff40630a325,

title = "Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions",

abstract = "An electron-deficient iron(III) porphyrin complex associated with iodobenzene diacetate (PhI(OAc)2) afforded high yields of oxygenated products in catalytic oxygenations of olefins and alkanes when the reactions were carried out in the presence of a small amount of water. An oxoiron(IV) porphyrin cation radical intermediate was generated in the reaction of an iron(III) porphyrin complex and PhI(OAc)2. These results demonstrate that PhI(OAc)2, which is soluble in organic media, safe to use, and readily available, is an efficient oxygen atom donor that can be used as a substitute for polymeric iodosylbenzene (PhIO) in metalloporphyrin-mediated oxygenation reactions.",

keywords = "Epoxidation, Hydroxylation, Iodobenzene diacetate, Iodosylbenzene, Iron(III) porphyrin",

author = "In, {Jun Hee} and Park, {Se Eun} and Rita Song and Wonwoo Nam",

note = "Funding Information: This research was supported by the Korea Science and Engineering Foundation (R03-2001-00028 to W.N. and R05-2000-0008 to R.S.), the Korea Research Foundation (DP0270), and Ewha Womans University (2000).",

year = "2003",

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doi = "10.1016/S0020-1693(02)01239-2",

language = "English",

volume = "343",

pages = "373--376",

journal = "Inorganica Chimica Acta",

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T1 - Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions

AU - In, Jun Hee

AU - Park, Se Eun

AU - Song, Rita

AU - Nam, Wonwoo

N1 - Funding Information: This research was supported by the Korea Science and Engineering Foundation (R03-2001-00028 to W.N. and R05-2000-0008 to R.S.), the Korea Research Foundation (DP0270), and Ewha Womans University (2000).

PY - 2003/1/30

Y1 - 2003/1/30

N2 - An electron-deficient iron(III) porphyrin complex associated with iodobenzene diacetate (PhI(OAc)2) afforded high yields of oxygenated products in catalytic oxygenations of olefins and alkanes when the reactions were carried out in the presence of a small amount of water. An oxoiron(IV) porphyrin cation radical intermediate was generated in the reaction of an iron(III) porphyrin complex and PhI(OAc)2. These results demonstrate that PhI(OAc)2, which is soluble in organic media, safe to use, and readily available, is an efficient oxygen atom donor that can be used as a substitute for polymeric iodosylbenzene (PhIO) in metalloporphyrin-mediated oxygenation reactions.

AB - An electron-deficient iron(III) porphyrin complex associated with iodobenzene diacetate (PhI(OAc)2) afforded high yields of oxygenated products in catalytic oxygenations of olefins and alkanes when the reactions were carried out in the presence of a small amount of water. An oxoiron(IV) porphyrin cation radical intermediate was generated in the reaction of an iron(III) porphyrin complex and PhI(OAc)2. These results demonstrate that PhI(OAc)2, which is soluble in organic media, safe to use, and readily available, is an efficient oxygen atom donor that can be used as a substitute for polymeric iodosylbenzene (PhIO) in metalloporphyrin-mediated oxygenation reactions.

KW - Epoxidation

KW - Hydroxylation

KW - Iodobenzene diacetate

KW - Iodosylbenzene

KW - Iron(III) porphyrin

UR - http://www.scopus.com/inward/record.url?scp=0037472444&partnerID=8YFLogxK

U2 - 10.1016/S0020-1693(02)01239-2

DO - 10.1016/S0020-1693(02)01239-2

M3 - Article

AN - SCOPUS:0037472444

SN - 0020-1693

VL - 343

SP - 373

EP - 376

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions

Abstract

Bibliographical note

Keywords

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