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AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes : Synthesis of 3,3-diarylpropenenitriles. / Gorbunova, Yelizaveta; Ryabukhin, Dmitry S.; Vasilyev, Aleksander V.

In: Beilstein Journal of Organic Chemistry, Vol. 17, 01.11.2021, p. 2663-2667.

Research output: Contribution to journal › Article › peer-review

Harvard

Gorbunova, Y, Ryabukhin, DS & Vasilyev, AV 2021, 'AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles', Beilstein Journal of Organic Chemistry, vol. 17, pp. 2663-2667. https://doi.org/10.3762/bjoc.17.180

APA

Gorbunova, Y., Ryabukhin, D. S., & Vasilyev, A. V. (2021). AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles. Beilstein Journal of Organic Chemistry, 17, 2663-2667. https://doi.org/10.3762/bjoc.17.180

Vancouver

Gorbunova Y, Ryabukhin DS, Vasilyev AV. AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles. Beilstein Journal of Organic Chemistry. 2021 Nov 1;17:2663-2667. https://doi.org/10.3762/bjoc.17.180

Author

Gorbunova, Yelizaveta ; Ryabukhin, Dmitry S. ; Vasilyev, Aleksander V. / AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes : Synthesis of 3,3-diarylpropenenitriles. In: Beilstein Journal of Organic Chemistry. 2021 ; Vol. 17. pp. 2663-2667.

BibTeX

@article{c19e39f5fe0a4c17939147c0fb75a8c0,
title = "AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles",
abstract = "Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3- diarylpropenenitriles (Ar(Ar')C=CHCN) in yields of 20-64%, as products of mainly anti-hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF3SO3H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55-70%. ",
keywords = "Aluminum bromide, Hydroarylation, Indenones, Propenenitriles, Propynenitriles, ACTIVATION, ANNULATION, indenones, aluminum bromide, propenenitriles, hydroarylation, propynenitriles, TRIFLUOROMETHANESULFONIC ACID",
author = "Yelizaveta Gorbunova and Ryabukhin, {Dmitry S.} and Vasilyev, {Aleksander V.}",
note = "Publisher Copyright: {\textcopyright} 2021 Gorbunova et al.",
year = "2021",
month = nov,
day = "1",
doi = "10.3762/bjoc.17.180",
language = "English",
volume = "17",
pages = "2663--2667",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes

T2 - Synthesis of 3,3-diarylpropenenitriles

AU - Gorbunova, Yelizaveta

AU - Ryabukhin, Dmitry S.

AU - Vasilyev, Aleksander V.

N1 - Publisher Copyright: © 2021 Gorbunova et al.

PY - 2021/11/1

Y1 - 2021/11/1

N2 - Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3- diarylpropenenitriles (Ar(Ar')C=CHCN) in yields of 20-64%, as products of mainly anti-hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF3SO3H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55-70%.

AB - Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3- diarylpropenenitriles (Ar(Ar')C=CHCN) in yields of 20-64%, as products of mainly anti-hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF3SO3H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55-70%.

KW - Aluminum bromide

KW - Hydroarylation

KW - Indenones

KW - Propenenitriles

KW - Propynenitriles

KW - ACTIVATION

KW - ANNULATION

KW - indenones

KW - aluminum bromide

KW - propenenitriles

KW - hydroarylation

KW - propynenitriles

KW - TRIFLUOROMETHANESULFONIC ACID

UR - http://www.scopus.com/inward/record.url?scp=85119924776&partnerID=8YFLogxK

U2 - 10.3762/bjoc.17.180

DO - 10.3762/bjoc.17.180

M3 - Article

AN - SCOPUS:85119924776

VL - 17

SP - 2663

EP - 2667

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 89276211