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

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• 作者：Toshifumi Dohi ; Motoki Ito ; Nobutaka Yamaoka ; Koji Morimoto ; Hiromichi Fujioka ; Yasuyuki Kita
• 关键词：Hypervalent iodine ; Single-electron-transfer ; Heteroaromatic compound ; Oxidation
• 刊名：Tetrahedron
• 出版年：2009
• 出版时间：26 December 2009
• 年：2009
• 卷：65
• 期：52
• 页码：10797-10815
• 全文大小：1141 K

文摘

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.