Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone®: Oxidation of p-Alkoxyphenols to p-Benzoquinones

被引：35

作者：

Yakura, Takayuki ^{[1
]}

Tian, Yuan ^{[1
]}

Yamauchi, Yu ^{[1
]}

Omoto, Masanori ^{[1
]}

Konishi, Tatsuya ^{[1
]}

机构：

[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Toyama 9300194, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2009年 / 57卷 / 03期

关键词：

hypervalent iodine; 4-iodophenoxyacetic acid; Oxone (R); p-alkoxyphenol; p-benzoquinone; M-CHLOROPERBENZOIC ACID; POLYMER-SUPPORTED IBX; IN-SITU GENERATION; TOLUENESULFONIC ACID; ALPHA-TOSYLOXYKETONES; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; OXIDIZING SYSTEM; RECENT PROGRESS; QUINONES;

D O I：

10.1248/cpb.57.252

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A catalytic hypervalent iodine oxidation of p-alkoxyphenols using 4-iodophenoxyacetic acid (1a) and Oxone (R) was developed. Reaction of p-alkoxyphenol (2) with a catalytic amount of la in the presence of Oxone (R) as a co-oxidant in 2,2,2-trifluoroethanol-water (1 : 2) gave the corresponding p-qui none (3) in excellent yield without special operation. The substituent effect on iodobenzene ring in the oxidation was observed; p-alkoxy is the most effective, with the series following the approximate order p-RO>p-Me. o-MeO, m-MeO>H>o-CO2H. And remarkable solvent effects were observed.

引用

页码：252 / 256

页数：5

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