Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

Yelizaveta Gorbunova; Dmitriy N. Zakusilo; Aleksander V. Vasilyev

doi:10.1016/j.tetlet.2019.02.047

Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

Yelizaveta Gorbunova, Dmitriy N. Zakusilo, Aleksander V. Vasilyev

Research output

Abstract

The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH ₂ CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

Original language	English
Article number	961-964
Journal	Tetrahedron Letters
Volume	60
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2019.02.047
Publication status	Published - 4 Apr 2019

Fingerprint

Carbon

Nitriles

Protonation

Reaction products

Temperature

cinnamonitrile

trifluoromethanesulfonic acid

propionitrile

Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Gorbunova, Y., Zakusilo, D. N., & Vasilyev, A. V. (2019). Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. Tetrahedron Letters, 60(14), [961-964]. https://doi.org/10.1016/j.tetlet.2019.02.047

Gorbunova, Yelizaveta ; Zakusilo, Dmitriy N. ; Vasilyev, Aleksander V. / Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. In: Tetrahedron Letters. 2019 ; Vol. 60, No. 14.

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title = "Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid",

abstract = "The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76{\%} yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.",

keywords = "Electrophilic substitution, Indanones, Nitriles, Superacids",

author = "Yelizaveta Gorbunova and Zakusilo, {Dmitriy N.} and Vasilyev, {Aleksander V.}",

year = "2019",

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Gorbunova, Y , Zakusilo, DN & Vasilyev, AV 2019, 'Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid', Tetrahedron Letters, vol. 60, no. 14, 961-964. https://doi.org/10.1016/j.tetlet.2019.02.047

Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. / Gorbunova, Yelizaveta ; Zakusilo, Dmitriy N.; Vasilyev, Aleksander V.

In: Tetrahedron Letters, Vol. 60, No. 14, 961-964, 04.04.2019.

Research output

TY - JOUR

T1 - Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

AU - Gorbunova, Yelizaveta

AU - Zakusilo, Dmitriy N.

AU - Vasilyev, Aleksander V.

PY - 2019/4/4

Y1 - 2019/4/4

N2 - The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

AB - The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

KW - Electrophilic substitution

KW - Indanones

KW - Nitriles

KW - Superacids

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U2 - 10.1016/j.tetlet.2019.02.047

DO - 10.1016/j.tetlet.2019.02.047

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VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters