Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’

A.N. Kazakova, R.O. Iakovenko, V.M. Muzalevskiy, I.A. Boyarskaya, M.S. Avdontceva, G.L. Starova, A.V. Vasilyev, V.G. Nenajdenko

Research output

12 Citations (Scopus)

Abstract

An unusual ‘dimerization’ of CF3-allyl alcohols [ArCHdouble bond; length as m-dashCHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar′H) led to CF3-alkenes [Ar(Ar′)CHCHdouble bond; length as m-dashCHCF3] in 48–75% yields. The mechanisms of the transformations are discussed.
Original languageEnglish
Pages (from-to)6851-6855
JournalTetrahedron Letters
Volume55
Issue number50
DOIs
Publication statusPublished - 2014

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Dimerization
Acids
Alkenes
Cations
allyl alcohol

Cite this

Kazakova, A.N. ; Iakovenko, R.O. ; Muzalevskiy, V.M. ; Boyarskaya, I.A. ; Avdontceva, M.S. ; Starova, G.L. ; Vasilyev, A.V. ; Nenajdenko, V.G. / Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 50. pp. 6851-6855.
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title = "Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’",
abstract = "An unusual ‘dimerization’ of CF3-allyl alcohols [ArCHdouble bond; length as m-dashCHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90{\%} yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar′H) led to CF3-alkenes [Ar(Ar′)CHCHdouble bond; length as m-dashCHCF3] in 48–75{\%} yields. The mechanisms of the transformations are discussed.",
keywords = "CF3-allyl alcohols, CF3-alkenes, Iron trichloride, Fluorinated indanes, CF3-allyl carbocations",
author = "A.N. Kazakova and R.O. Iakovenko and V.M. Muzalevskiy and I.A. Boyarskaya and M.S. Avdontceva and G.L. Starova and A.V. Vasilyev and V.G. Nenajdenko",
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Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’. / Kazakova, A.N.; Iakovenko, R.O.; Muzalevskiy, V.M.; Boyarskaya, I.A.; Avdontceva, M.S.; Starova, G.L.; Vasilyev, A.V.; Nenajdenko, V.G.

In: Tetrahedron Letters, Vol. 55, No. 50, 2014, p. 6851-6855.

Research output

TY - JOUR

T1 - Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’

AU - Kazakova, A.N.

AU - Iakovenko, R.O.

AU - Muzalevskiy, V.M.

AU - Boyarskaya, I.A.

AU - Avdontceva, M.S.

AU - Starova, G.L.

AU - Vasilyev, A.V.

AU - Nenajdenko, V.G.

PY - 2014

Y1 - 2014

N2 - An unusual ‘dimerization’ of CF3-allyl alcohols [ArCHdouble bond; length as m-dashCHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar′H) led to CF3-alkenes [Ar(Ar′)CHCHdouble bond; length as m-dashCHCF3] in 48–75% yields. The mechanisms of the transformations are discussed.

AB - An unusual ‘dimerization’ of CF3-allyl alcohols [ArCHdouble bond; length as m-dashCHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar′H) led to CF3-alkenes [Ar(Ar′)CHCHdouble bond; length as m-dashCHCF3] in 48–75% yields. The mechanisms of the transformations are discussed.

KW - CF3-allyl alcohols

KW - CF3-alkenes

KW - Iron trichloride

KW - Fluorinated indanes

KW - CF3-allyl carbocations

U2 - 10.1016/j.tetlet.2014.10.083

DO - 10.1016/j.tetlet.2014.10.083

M3 - Article

VL - 55

SP - 6851

EP - 6855

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -