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Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides

Oleg Vladimirovich Khazipov 1
Oleg Vladimirovich Khazipov
, 
Anastasia Sergeevna Pyatachenko 1
Anastasia Sergeevna Pyatachenko
, 
Daria Viktorovna Chernysheva 1
Daria Viktorovna Chernysheva
, 
Viktor Mikhailovich Chernyshev 1
Viktor Mikhailovich Chernyshev
10.71267/mencom.7937
Published 2026-03-24
Communication , Volume 36, Issue 3, 276-278
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Khazipov O. V. et al. Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 276-278.
GOST all authors (up to 50) Copy
Khazipov O. V., Pyatachenko A. S., Chernysheva D. V., Chernyshev V. M. Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 276-278.
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TY - JOUR
DO - 10.71267/mencom.7937
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7937
TI - Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides
T2 - Mendeleev Communications
AU - Khazipov, Oleg Vladimirovich
AU - Pyatachenko, Anastasia Sergeevna
AU - Chernysheva, Daria Viktorovna
AU - Chernyshev, Viktor Mikhailovich
PY - 2026
DA - 2026/03/24
PB - Mendeleev Communications
SP - 276-278
IS - 3
VL - 36
ER -
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@article{2026_Khazipov,
author = {Oleg Vladimirovich Khazipov and Anastasia Sergeevna Pyatachenko and Daria Viktorovna Chernysheva and Viktor Mikhailovich Chernyshev},
title = {Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7937},
number = {3},
pages = {276--278},
doi = {10.71267/mencom.7937}
}
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Khazipov, Oleg Vladimirovich, et al. “Thermally activated (NHC)NiCp2 precatalysts for the cross-coupling of amines with aryl chlorides.” Mendeleev Communications, vol. 36, no. 3, Mar. 2026, pp. 276-278. https://mendcomm.colab.ws/publications/10.71267/mencom.7937.
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Keywords

amines
aryl chlorides
C–N cross-coupling
cyclopentadienyl
N-heterocyclic carbene
nickel complexes

Abstract

Readily accessible (NHC)NiCp2 complexes were identified as efficient thermally activated precatalysts for the C–N cross-coupling reaction between unactivated aryl chlorides and anilines or secondary aliphatic amines. The optimized catalytic system enables the selective coupling of sterically hindered partners and tolerates fluoride substituents in the aromatic rings.

Funders

Ministry of Education and Science of the Russian Federation
075-03-2024-152/1

References

1.
Efficient C–N and C–S Bond Formation Using the Highly Active [Ni(allyl)Cl(IPr*OMe)] Precatalyst
Martin A.R., Nelson D.J., Meiries S., Slawin A.M., Nolan S.P.
European Journal of Organic Chemistry, 2014
2.
Nickel‐Catalysed Amination of Arenes and Heteroarenes
Philip R.M., Veetil Saranya P., Anilkumar G.
European Journal of Organic Chemistry, 2022
3.
Metal–N-Heterocyclic Carbene Complexes in Buchwald–Hartwig Amination Reactions
Bera S.S., Utecht-Jarzyńska G., Yang S., Nolan S.P., Szostak M.
Chemical Reviews, 2025
5.
Nickel-Catalyzed Amination of Aryl Chlorides with Amides
Li J., Huang C., Wen D., Zheng Q., Tu B., Tu T.
Organic Letters, 2020
7.
Synthesis, Structural Characterization, and Catalytic Activity of IPrNi(styrene)2in the Amination of Aryl Tosylates
Iglesias M.J., Blandez J.F., Fructos M.R., Prieto A., Álvarez E., Belderrain T.R., Nicasio M.C.
Organometallics, 2012
8.
CN Coupling of Indoles and Carbazoles with Aromatic Chlorides Catalyzed by a Single-Component NHC-Nickel(0) Precursor
Rull S.G., Blandez J.F., Fructos M.R., Belderrain T.R., Nicasio M.C.
Advanced Synthesis and Catalysis, 2015
9.
Phosphine-functionalized NHC Ni(ii) and Ni(0) complexes: synthesis, characterization and catalytic properties
Rull S.G., Rama R.J., Álvarez E., Fructos M.R., Belderrain T.R., Nicasio M.C.
Dalton Transactions, 2017
10.
Elucidating the Mechanism of Aryl Aminations Mediated by NHC-Supported Nickel Complexes: Evidence for a Nonradical Ni(0)/Ni(II) Pathway
Rull S.G., Funes-Ardoiz I., Maya C., Maseras F., Fructos M.R., Belderrain T.R., Nicasio M.C.
ACS Catalysis, 2018
12.
Nickel-catalyzed amination of aryl pivalates by the cleavage of aryl C-O bonds.
Shimasaki T., Tobisu M., Chatani N.
Angewandte Chemie - International Edition, 2010
13.
Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbon‒oxygen bonds
Tobisu M., Yasutome A., Yamakawa K., Shimasaki T., Chatani N.
Tetrahedron, 2012
15.
Stable, Well-Defined Nickel(0) Catalysts for Catalytic C–C and C–N Bond Formation
Nett A.J., Cañellas S., Higuchi Y., Robo M.T., Kochkodan J.M., Haynes M.T., Kampf J.W., Montgomery J.
ACS Catalysis, 2018
16.
Nickel-catalysed amination of aryl chlorides using a dihydroimidazoline carbene ligand
Gradel B., Brenner E., Schneider R., Fort Y.
Tetrahedron Letters, 2001
17.
Nickel(0)/Dihydroimidazol-2-ylidene Complex Catalyzed Coupling of Aryl Chlorides and Amines
Desmarets C., Schneider R., Fort Y.
Journal of Organic Chemistry, 2002
18.
Nickel-Catalyzed Amination of Aryl Sulfamates and Carbamates Using an Air-Stable Precatalyst
Hie L., Ramgren S.D., Mesganaw T., Garg N.K.
Organic Letters, 2012
19.
Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF
Fine Nathel N.F., Kim J., Hie L., Jiang X., Garg N.K.
ACS Catalysis, 2014
22.
Simple Synthesis of CpNi(NHC)Cl Complexes (Cp = Cyclopentadienyl; NHC = N-Heterocyclic Carbene)
Kelly R.A., Scott N.M., Díez-González S., Stevens E.D., Nolan S.P.
Organometallics, 2005
23.
Bench-Stable N -Heterocyclic Carbene Nickel Precatalysts for C−C and C−N Bond-Forming Reactions
Strieth-Kalthoff F., Longstreet A.R., Weber J.M., Jamison T.F.
ChemCatChem, 2018
25.
A Modular, Air-Stable Nickel Precatalyst
Shields J.D., Gray E.E., Doyle A.G.
Organic Letters, 2015
26.
Practical, Large-Scale Preparation of Ni(tmeda)(o-tol)Cl
John M.E., Foster D., Moggach S.A., Koutsantonis G.A., Dorta R., Stewart S.G.
Organic Process Research and Development, 2024
27.
Bench-Stable Nickel Precatalysts with Heck-type Activation
Weber J.M., Longstreet A.R., Jamison T.F.
Organometallics, 2018