AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar′H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr(3), 6 equiv) at room temperature for 0.5–2 h result in the stereoselective formation of 3,3-diarylpropenenitriles (Ar(Ar′)C=CHCN) in yi...

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Autores principales: Gorbunova, Yelizaveta, Ryabukhin, Dmitry S, Vasilyev, Aleksander V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576820/
https://www.ncbi.nlm.nih.gov/pubmed/34804238
http://dx.doi.org/10.3762/bjoc.17.180
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author Gorbunova, Yelizaveta
Ryabukhin, Dmitry S
Vasilyev, Aleksander V
author_facet Gorbunova, Yelizaveta
Ryabukhin, Dmitry S
Vasilyev, Aleksander V
author_sort Gorbunova, Yelizaveta
collection PubMed
description Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar′H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr(3), 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 CF(3)SO(3)H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55–70%.
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spelling pubmed-85768202021-11-18 AlBr(3)-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 Beilstein J Org Chem Full Research Paper Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar′H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr(3), 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 CF(3)SO(3)H (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55–70%. Beilstein-Institut 2021-11-01 /pmc/articles/PMC8576820/ /pubmed/34804238 http://dx.doi.org/10.3762/bjoc.17.180 Text en Copyright © 2021, Gorbunova et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Gorbunova, Yelizaveta
Ryabukhin, Dmitry S
Vasilyev, Aleksander V
AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title_full AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title_fullStr AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title_full_unstemmed AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title_short AlBr(3)-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
title_sort albr(3)-promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576820/
https://www.ncbi.nlm.nih.gov/pubmed/34804238
http://dx.doi.org/10.3762/bjoc.17.180
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