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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
Publication type: Journal Article
Publication date: 2021-11-01
scimago Q2
wos Q3
SJR: 0.482
CiteScore: 3.8
Impact factor: 2.1
ISSN: 18605397
PubMed ID:
34804238
Organic Chemistry
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%.
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Gorbunova Y. et al. 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. Vol. 17. pp. 2663-2667.
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Gorbunova Y., Vasilyev A. V., Ryabukhin D. S. 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. Vol. 17. pp. 2663-2667.
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TY - JOUR
DO - 10.3762/bjoc.17.180
UR - https://doi.org/10.3762/bjoc.17.180
TI - AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles
T2 - Beilstein Journal of Organic Chemistry
AU - Gorbunova, Yelizaveta
AU - Vasilyev, Aleksander V
AU - Ryabukhin, Dmitry S.
PY - 2021
DA - 2021/11/01
PB - Beilstein-Institut
SP - 2663-2667
VL - 17
PMID - 34804238
SN - 1860-5397
ER -
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@article{2021_Gorbunova,
author = {Yelizaveta Gorbunova and Aleksander V Vasilyev and Dmitry S. Ryabukhin},
title = {AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles},
journal = {Beilstein Journal of Organic Chemistry},
year = {2021},
volume = {17},
publisher = {Beilstein-Institut},
month = {nov},
url = {https://doi.org/10.3762/bjoc.17.180},
pages = {2663--2667},
doi = {10.3762/bjoc.17.180}
}