- A novel and direct synthesis of alkylated 2,2′-bithiophene derivatives using a combination of hypervalent iodine(III) reagent and BF3·Et2O
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A novel nonmetallic oxidative coupling of alkylthiophene derivatives leading to the corresponding 2,2′-bithiophene derivatives using a combination of a hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and BF3·Et2O was developed.
- Tohma, Hirofumi,Iwata, Minako,Maegawa, Tomohiro,Kiyono, Yorito,Maruyama, Akinobu,Kita, Yasuyuki
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- Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
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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.
- Dohi, Toshifumi,Ito, Motoki,Yamaoka, Nobutaka,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
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experimental part
p. 10797 - 10815
(2010/03/01)
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- The synthesis of head-to-tail (H-T) dimers of 3-substituted thiophenes by the hypervalent iodine(III)-induced oxidative biaryl coupling reaction
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The head-to-tail (H-T) dimers could be obtained selectively by the oxidative coupling reaction of 3-substituted thiophenes using a combination of hypervalent iodine(III) reagents and trimethylsilyl trifluoromethanesulfonate. The Roval Society of Chemistry 2005.
- Dohi, Toshifumi,Morimoto, Koji,Kiyono, Yorito,Maruyama, Akinobu,Tohma, Hirofumi,Kita, Yasuyuki
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p. 2930 - 2932
(2007/10/03)
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