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Issue 12, 2017
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Acid-promoted cyclization of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers into CF3-indenes

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Abstract

2,4-Diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers in H2SO4 at room temperature in just 2 min are quantitatively cyclized into 1-aryl-3-trifluoromethyl-1H-indenes. The reaction proceeds through an intermediate formation of the corresponding CF3-allyl cations, which are cyclized regioselectively at the allyl carbon atom most remote from the CF3-group. The obtained CF3-indenes in solution of EtOAc in the presence of silica gel at room temperature over 4 h are quantitatively isomerized into 3-aryl-1-trifluoromethyl-1H-indenes.

Graphical abstract: Acid-promoted cyclization of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers into CF3-indenes

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Publication details

The article was received on 18 Feb 2017, accepted on 27 Feb 2017 and first published on 27 Feb 2017


Article type: Paper
DOI: 10.1039/C7OB00406K
Citation: Org. Biomol. Chem., 2017,15, 2541-2550
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    Acid-promoted cyclization of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers into CF3-indenes

    M. Yu. Martynov, R. O. Iakovenko, A. N. Kazakova, I. A. Boyarskaya and A. V. Vasilyev, Org. Biomol. Chem., 2017, 15, 2541
    DOI: 10.1039/C7OB00406K

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