Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent |
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Authors: | Toshifumi Dohi Motoki Ito Koji Morimoto Yasuyuki Kita |
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Affiliation: | a College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan |
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Abstract: | 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. |
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Keywords: | Hypervalent iodine Single-electron-transfer Heteroaromatic compound Oxidation |
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