Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®

Takayuki Yakura; Yû Yamauchi; Yuan Tian; Masanori Omoto

doi:10.1248/cpb.56.1632

Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®

Takayuki Yakura^*, Yû Yamauchi, Yuan Tian, Masanori Omoto

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

36 被引用数 (Scopus)

抄録

A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO₅·KHSO ₄·K₂SO₄ (Oxone®) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone® as a co-oxidant in 2,2,2-trifluoroethanol-water (1:2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.

本文言語	英語
ページ（範囲）	1632-1634
ページ数	3
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	56
号	11
DOI	https://doi.org/10.1248/cpb.56.1632
出版ステータス	出版済み - 2008

ASJC Scopus 主題領域

化学一般
創薬

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10.1248/cpb.56.1632

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title = "Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone{\textregistered}",

abstract = "A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO5·KHSO 4·K2SO4 (Oxone{\textregistered}) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone{\textregistered} as a co-oxidant in 2,2,2-trifluoroethanol-water (1:2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.",

keywords = "4-Iodophenoxyacetic acid, Blattellaquinone, Catalytic hypervalent iodine oxidation, Oxone{\textregistered}, p-dialkoxybenzene, p-quinone",

author = "Takayuki Yakura and Y{\^u} Yamauchi and Yuan Tian and Masanori Omoto",

year = "2008",

doi = "10.1248/cpb.56.1632",

language = "英語",

volume = "56",

pages = "1632--1634",

journal = "Chemical and Pharmaceutical Bulletin",

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publisher = "Pharmaceutical Society of Japan",

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T1 - Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®

AU - Yakura, Takayuki

AU - Yamauchi, Yû

AU - Tian, Yuan

AU - Omoto, Masanori

PY - 2008

Y1 - 2008

N2 - A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO5·KHSO 4·K2SO4 (Oxone®) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone® as a co-oxidant in 2,2,2-trifluoroethanol-water (1:2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.

AB - A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO5·KHSO 4·K2SO4 (Oxone®) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone® as a co-oxidant in 2,2,2-trifluoroethanol-water (1:2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.

KW - 4-Iodophenoxyacetic acid

KW - Blattellaquinone

KW - Catalytic hypervalent iodine oxidation

KW - Oxone®

KW - p-dialkoxybenzene

KW - p-quinone

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U2 - 10.1248/cpb.56.1632

DO - 10.1248/cpb.56.1632

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SN - 0009-2363

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Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®

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