Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent

被引：213

作者：

Dohi, Toshifumi ^{[1
,2
]}

Ito, Motoki ^{[2
]}

Yamaoka, Nobutaka ^{[1
]}

Morimoto, Koji ^{[1
]}

Fujioka, Hiromichi ^{[2
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Shiga 5258577, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 52期

关键词：

Hypervalent iodine; Single-electron-transfer; Heteroaromatic compound; Oxidation; PHENOL ETHER DERIVATIVES; BIARYL COUPLING REACTION; METHYL-SUBSTITUTED 2,2'-BIPYRROLES; PYRROLOIMINOQUINONE MARINE PRODUCT; PYRIDINIUM POLYHYDROGEN FLUORIDE; DESS-MARTIN PERIODINANE; AZIDO SIDE-CHAIN; ORGANIC-SYNTHESIS; INTRAMOLECULAR CYCLIZATION; ANODIC CYANATION;

D O I：

10.1016/j.tet.2009.10.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In 1994, we first determined the single-electron-transfer (SET) oxidation ability of phenyliodine(III) bis(trifluoroacetate) (PIFA) toward phenyl ethers, affording the corresponding aromatic cation radicals. Since then, hypervalent iodine(III) has been utilized as a selective and efficient SET oxidizing agent that enables a variety of direct C-H functionalizations of aromatic rings in electron-rich arenes under mild conditions. We have now extended the original method to work in a series of heteroaromatic compounds such as thiophenes, pyrroles, and indoles. The investigations and results obtained since the start of this century are summarized in this article. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：10797 / 10815

页数：19

共 213 条

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