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Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding

Alexey Sergeevich Galushko 1
Alexey Sergeevich Galushko
, 
Mariya Vladimirovna Grudova 1
Mariya Vladimirovna Grudova
, 
Vladimir A Skuratovich 1
Vladimir A Skuratovich
, 
Valentina Victorovna Ilyushenkova 1
Valentina Victorovna Ilyushenkova
10.71267/mencom.7700
Published 2025-05-21
Communication , Volume 35, Issue 4, 430-432
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Galushko A. S. et al. Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 430-432.
GOST all authors (up to 50) Copy
Galushko A. S., Grudova M. V., Skuratovich V. A., Ilyushenkova V. V. Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 430-432.
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TY - JOUR
DO - 10.71267/mencom.7700
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7700
TI - Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding
T2 - Mendeleev Communications
AU - Galushko, Alexey Sergeevich
AU - Grudova, Mariya Vladimirovna
AU - Skuratovich, Vladimir A
AU - Ilyushenkova, Valentina Victorovna
PY - 2025
DA - 2025/05/21
PB - Mendeleev Communications
SP - 430-432
IS - 4
VL - 35
ER -
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@article{2025_Galushko,
author = {Alexey Sergeevich Galushko and Mariya Vladimirovna Grudova and Vladimir A Skuratovich and Valentina Victorovna Ilyushenkova},
title = {Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7700},
number = {4},
pages = {430--432},
doi = {10.71267/mencom.7700}
}
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Galushko, Alexey Sergeevich, et al. “Effect of steric hindrance of N-heterocyclic carbene in a copper complex on the efficiency of the Chan--Evans--Lam reaction proceeding.” Mendeleev Communications, vol. 35, no. 4, May. 2025, pp. 430-432. https://mendcomm.colab.ws/publications/10.71267/mencom.7700.

Keywords

arylation
Chan�Evans�Lam reaction
cross-coupling
NHC carbene
steric hindrance.

Abstract

This work investigates the effect of the steric hindrance of the NHC ligand in the NHC-CuCl complex on the Chan-Evans-Lam reaction between PhB(OH)2 and PhNH2 affording Ph2NH. The primary reaction products of PhB(OH)2 with NHC ligands such as BIMe, IMes, and IPr were obtained for the first time, showing that reducing steric hindrance improves the yield of Ph2NH and decreases side reactions. However, complete absence of steric shielding around copper prevents product formation.

Funders

Russian Science Foundation
23-13-00171