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Issue 5, 2019
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HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF3-indenes and DFT study of intermediate carbocations

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Abstract

The reaction of CF3-propargyl alcohols [ArC[triple bond, length as m-dash]CCH(OH)CF3] with arenes under the action of acidic HUSY zeolite CBV-720 was investigated. It was found that the reaction at 100 °C for 1 h gave rise to 3-aryl-1-CF3-indenes in up to 83% yield. Electronic characteristics of the reaction key intermediates, mesomeric CF3-propargyl-allenyl cations [ArC[triple bond, length as m-dash]C−HC+(CF3) ↔ ArC+[double bond, length as m-dash]C[double bond, length as m-dash]CH(CF3)], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.

Graphical abstract: HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF3-indenes and DFT study of intermediate carbocations

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Publication details

The article was received on 19 Nov 2018, accepted on 10 Jan 2019 and first published on 10 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02887G
Citation: Org. Biomol. Chem., 2019,17, 1215-1224

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    HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF3-indenes and DFT study of intermediate carbocations

    S. K. Nursahedova, A. V. Zerov, I. A. Boyarskaya, E. V. Grinenko, V. G. Nenajdenko and A. V. Vasilyev, Org. Biomol. Chem., 2019, 17, 1215
    DOI: 10.1039/C8OB02887G

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