Iridium-Catalyzed C(sp3)−H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans

Toshimichi Ohmura, Satoshi Kusaka, Takeru Torigoe, Michinori Suginome

Research output: Contribution to journalArticle

Abstract

Intramolecular addition of an O-methyl C(sp3)−H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)−H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).

Original languageEnglish
Pages (from-to)4448-4453
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number19
DOIs
Publication statusPublished - Oct 8 2019
Externally publishedYes

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Phenyl Ethers
Methyl Ethers
Iridium
Ethers
Carbon
Toluene
Derivatives
Catalysts
coumaran

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Iridium-Catalyzed C(sp3)−H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans. / Ohmura, Toshimichi; Kusaka, Satoshi; Torigoe, Takeru; Suginome, Michinori.

In: Advanced Synthesis and Catalysis, Vol. 361, No. 19, 08.10.2019, p. 4448-4453.

Research output: Contribution to journalArticle

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abstract = "Intramolecular addition of an O-methyl C(sp3)−H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)−H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96{\%} ee. (Figure presented.).",
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