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TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

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Abstract

The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes in good yields (up to 99%). The predominant or exclusive formation of indanes with a trans-configuration of 1,3-diaryl groups has been observed. The reaction proceeds through an intermediate formation of the corresponding mesomeric CF3-allyl cations. A plausible reaction mechanism is discussed.

Graphical abstract: TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

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Publication details

The article was received on 27 Jun 2019, accepted on 04 Aug 2019 and first published on 05 Aug 2019


Article type: Research Article
DOI: 10.1039/C9QO00822E
Org. Chem. Front., 2019, Advance Article

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    TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

    A. V. Zerov, A. A. Bulova, O. V. Khoroshilova and A. V. Vasilyev, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00822E

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