Development of novel catalytic system, iodoarene-Oxone®, on hypervalent iodine oxidation of phenols and alcohols

Takayuki Yakura; Hisanori Nambu; Tomoya Fujiwara

doi:10.5059/yukigoseikyokaishi.75.209

Development of novel catalytic system, iodoarene-Oxone®, on hypervalent iodine oxidation of phenols and alcohols

Takayuki Yakura, Hisanori Nambu, Tomoya Fujiwara

Synthetic and Biomolecular Organic Chemistry

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

1 Scopus citations

Abstract

Catalytic hypervalent iodine oxidation reactions of phenols and alcohols with iodoarene-Oxone® system were developed. Oxone® (2KHSO₅ · KHSO₄ · K₂SO₄) is well known as a safe and inexpensive oxidant. 4-Iodophenoxyacetic acid (IPAA) is efficient for the phenol oxidations. IPAA is commercially available and it is so soluble with a weak alkaline solution, such as saturated sodium bicarbonate solution, that it is easy separable from the product. 2-Iodobenzamide (IBamide) is efficient for the alcohol oxidations. The oxidation reaction using IBamide with Oxone® can be carried out at room temperature. The catalytic activity of IBamide is lower than that of 2-iodobenzoic acid at 70 °C, whereas higher at room temperature.

Original language	English
Pages (from-to)	209-218
Number of pages	10
Journal	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume	75
Issue number	3
DOIs	https://doi.org/10.5059/yukigoseikyokaishi.75.209
State	Published - 2017

Keywords

2-iodobenzamide
4-iodophenoxyacetic acid
Alcohols
Hypervalent iodine
Oxone®
Phenols

ASJC Scopus subject areas

Organic Chemistry

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10.5059/yukigoseikyokaishi.75.209

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title = "Development of novel catalytic system, iodoarene-Oxone{\textregistered}, on hypervalent iodine oxidation of phenols and alcohols",

abstract = "Catalytic hypervalent iodine oxidation reactions of phenols and alcohols with iodoarene-Oxone{\textregistered} system were developed. Oxone{\textregistered} (2KHSO5 · KHSO4 · K2SO4) is well known as a safe and inexpensive oxidant. 4-Iodophenoxyacetic acid (IPAA) is efficient for the phenol oxidations. IPAA is commercially available and it is so soluble with a weak alkaline solution, such as saturated sodium bicarbonate solution, that it is easy separable from the product. 2-Iodobenzamide (IBamide) is efficient for the alcohol oxidations. The oxidation reaction using IBamide with Oxone{\textregistered} can be carried out at room temperature. The catalytic activity of IBamide is lower than that of 2-iodobenzoic acid at 70 °C, whereas higher at room temperature.",

keywords = "2-iodobenzamide, 4-iodophenoxyacetic acid, Alcohols, Hypervalent iodine, Oxone{\textregistered}, Phenols",

author = "Takayuki Yakura and Hisanori Nambu and Tomoya Fujiwara",

year = "2017",

doi = "10.5059/yukigoseikyokaishi.75.209",

language = "英語",

volume = "75",

pages = "209--218",

journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",

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publisher = "Society of Synthetic Organic Chemistry",

number = "3",

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TY - JOUR

T1 - Development of novel catalytic system, iodoarene-Oxone®, on hypervalent iodine oxidation of phenols and alcohols

AU - Yakura, Takayuki

AU - Nambu, Hisanori

AU - Fujiwara, Tomoya

PY - 2017

Y1 - 2017

N2 - Catalytic hypervalent iodine oxidation reactions of phenols and alcohols with iodoarene-Oxone® system were developed. Oxone® (2KHSO5 · KHSO4 · K2SO4) is well known as a safe and inexpensive oxidant. 4-Iodophenoxyacetic acid (IPAA) is efficient for the phenol oxidations. IPAA is commercially available and it is so soluble with a weak alkaline solution, such as saturated sodium bicarbonate solution, that it is easy separable from the product. 2-Iodobenzamide (IBamide) is efficient for the alcohol oxidations. The oxidation reaction using IBamide with Oxone® can be carried out at room temperature. The catalytic activity of IBamide is lower than that of 2-iodobenzoic acid at 70 °C, whereas higher at room temperature.

AB - Catalytic hypervalent iodine oxidation reactions of phenols and alcohols with iodoarene-Oxone® system were developed. Oxone® (2KHSO5 · KHSO4 · K2SO4) is well known as a safe and inexpensive oxidant. 4-Iodophenoxyacetic acid (IPAA) is efficient for the phenol oxidations. IPAA is commercially available and it is so soluble with a weak alkaline solution, such as saturated sodium bicarbonate solution, that it is easy separable from the product. 2-Iodobenzamide (IBamide) is efficient for the alcohol oxidations. The oxidation reaction using IBamide with Oxone® can be carried out at room temperature. The catalytic activity of IBamide is lower than that of 2-iodobenzoic acid at 70 °C, whereas higher at room temperature.

KW - 2-iodobenzamide

KW - 4-iodophenoxyacetic acid

KW - Alcohols

KW - Hypervalent iodine

KW - Oxone®

KW - Phenols

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U2 - 10.5059/yukigoseikyokaishi.75.209

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M3 - 学術論文

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JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

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ER -

Development of novel catalytic system, iodoarene-Oxone®, on hypervalent iodine oxidation of phenols and alcohols

Abstract

Keywords

ASJC Scopus subject areas

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