Regioselective Annulation of 2‐(2‐Bromophenyl)‐ <scp>1</scp> <i>H</i> ‐Imidazoles With <i>Ortho</i> ‐Substituted Phenylacetylenes Catalyzed by <scp>CuI</scp>

ABSTRACT The two‐component reaction between 2‐(2‐bromophenyl)‐1 H ‐imidazoles and ortho ‐substituted phenylacetylenes was investigated under basic conditions catalyzed by CuI. High yields of 5‐benzylidene‐5 H ‐imidazo[2,1‐ a ]isoindoles were obtained via a 5‐exo‐dig reaction when the substituent was an electron‐withdrawing group. Conversely, when the substituent was an electron‐donating group, the reaction yielded 5‐arylimidazo[2,1‐ a ]isoquinolines through a 6‐endo‐dig process.

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Publication Details

Journal
Journal of Heterocyclic Chemistry
Published
2026-01-20
DOI
https://doi.org/10.1002/jhet.70162
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Regioselective Annulation of 2‐(2‐Bromophenyl)‐ 1 H ‐Imidazoles With Ortho ‐Substituted Phenylacetylenes Catalyzed by CuI

Lanlan Lv, Lu‐Yi Wang, Yu‐Tong Zhai, Xiang‐Shan Wang et al.
Journal of Heterocyclic Chemistry
Catalytic C–H Functionalization Methods
article

Regioselective Annulation of 2‐(2‐Bromophenyl)‐ 1 H ‐Imidazoles With Ortho ‐Substituted Phenylacetylenes Catalyzed by CuI

Lanlan Lv, Lu‐Yi Wang, Yu‐Tong Zhai, Xiang‐Shan Wang, Kang‐Hao Zhang, Si‐Han Tang
article en

Abstract

ABSTRACT The two‐component reaction between 2‐(2‐bromophenyl)‐1 H ‐imidazoles and ortho ‐substituted phenylacetylenes was investigated under basic conditions catalyzed by CuI. High yields of 5‐benzylidene‐5 H ‐imidazo[2,1‐ a ]isoindoles were obtained via a 5‐exo‐dig reaction when the substituent was an electron‐withdrawing group. Conversely, when the substituent was an electron‐donating group, the reaction yielded 5‐arylimidazo[2,1‐ a ]isoquinolines through a 6‐endo‐dig process.

Journal of Heterocyclic Chemistry
Jiangsu Normal University (CN)
Openalex Percentile: Top 83%
Catalytic C–H Functionalization Methods
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