HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: Synthesis of CF 3 -indenes and DFT study of intermediate carbocations

Selbi K. Nursahedova, Aleksey V. Zerov, Irina A. Boyarskaya, Elena V. Grinenko, Valentine G. Nenajdenko, Aleksander V. Vasilyev

Research output

3 Citations (Scopus)

Abstract

The reaction of CF 3 -propargyl alcohols [ArCCCH(OH)CF 3 ] 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-CF 3 -indenes in up to 83% yield. Electronic characteristics of the reaction key intermediates, mesomeric CF 3 -propargyl-allenyl cations [ArCC-HC + (CF 3 ) ↔ ArC + CCH(CF 3 )], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)1215-1224
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number5
DOIs
Publication statusPublished - 1 Jan 2019

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Indenes
indene
Zeolites
Discrete Fourier transforms
Cations
alcohols
synthesis
cations
propargyl alcohol
electronics

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: Synthesis of CF 3 -indenes and DFT study of intermediate carbocations",
abstract = "The reaction of CF 3 -propargyl alcohols [ArCCCH(OH)CF 3 ] 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-CF 3 -indenes in up to 83{\%} yield. Electronic characteristics of the reaction key intermediates, mesomeric CF 3 -propargyl-allenyl cations [ArCC-HC + (CF 3 ) ↔ ArC + CCH(CF 3 )], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.",
author = "Nursahedova, {Selbi K.} and Zerov, {Aleksey V.} and Boyarskaya, {Irina A.} and Grinenko, {Elena V.} and Nenajdenko, {Valentine G.} and Vasilyev, {Aleksander V.}",
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TY - JOUR

T1 - HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes

T2 - Synthesis of CF 3 -indenes and DFT study of intermediate carbocations

AU - Nursahedova, Selbi K.

AU - Zerov, Aleksey V.

AU - Boyarskaya, Irina A.

AU - Grinenko, Elena V.

AU - Nenajdenko, Valentine G.

AU - Vasilyev, Aleksander V.

PY - 2019/1/1

Y1 - 2019/1/1

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AB - The reaction of CF 3 -propargyl alcohols [ArCCCH(OH)CF 3 ] 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-CF 3 -indenes in up to 83% yield. Electronic characteristics of the reaction key intermediates, mesomeric CF 3 -propargyl-allenyl cations [ArCC-HC + (CF 3 ) ↔ ArC + CCH(CF 3 )], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.

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