Home / Publications / Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes

Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes

Ivan A. Bidusenko 1
Ivan A. Bidusenko
, 
Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Nadezhda Il'inichna Protsuk 1
Nadezhda Il'inichna Protsuk
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2023.01.007
Published 2022-12-26
Communication , Volume 33, Issue 1, 24-26
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Bidusenko I. A. et al. Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 24-26.
GOST all authors (up to 50) Copy
Bidusenko I. A., Schmidt E. Y., Protsuk N. I., Ushakov I. A., Trofimov B. A. Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 24-26.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.007
TI - Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes
T2 - Mendeleev Communications
AU - Bidusenko, Ivan A.
AU - Schmidt, Elena Yur'evna
AU - Protsuk, Nadezhda Il'inichna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 24-26
IS - 1
VL - 33
ER -
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@article{2022_Bidusenko,
author = {Ivan A. Bidusenko and Elena Yur'evna Schmidt and Nadezhda Il'inichna Protsuk and Igor Alekseevich Ushakov and Boris Aleksandrovich Trofimov},
title = {Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.007},
number = {1},
pages = {24--26},
doi = {10.1016/j.mencom.2023.01.007}
}
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Bidusenko, Ivan A., et al. “Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 24-26. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.007.
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Keywords

acetylenes
ethynylation
imines
pyrroles
pyrrolines.
superbases
vinylation

Abstract

N-Benzyl aldimines react with arylacetylenes in the presence of ButOK/DMSO superbase system to afford 2,3,5-triaryl-1-pyrrolines as two tautomers with 1,2- and 1,5-location of the double bond, both being the trans-diastereomers. This version of the C=N bond ethynylation differs from the previous one with N-benzyl ketimines. The oxidation of the pyrroline tautomeric mixtures without their isolation gives 2,3,5-triaryl-1H-pyrroles.

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