Home / Publications / A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines

A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines

, 
Daria Sergeevna Kuliukhina 1
Daria Sergeevna Kuliukhina
, 
Alexei Dmitrievich Averin 1
Alexei Dmitrievich Averin
, 
Anton Sergeevich Abel 1
Anton Sergeevich Abel
, 
Evgenii Nikolaevich Savelyev 2
Evgenii Nikolaevich Savelyev
,  ,  , 
Carlos R.D. Correia 3
Carlos R.D. Correia
, 
10.1016/j.mencom.2022.01.029
Published 2022-01-03
Communication , Volume 32, Issue 1, 91-93
14
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Murashkina A. V. et al. A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 91-93.
GOST all authors (up to 50) Copy
Murashkina A. V., Kuliukhina D. S., Averin A. D., Abel A. S., Savelyev E. N., Orlinson B. S., Novakov I. A., Correia C. R., Beletskaya I. P. A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 91-93.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2022.01.029
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.029
TI - A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines
T2 - Mendeleev Communications
AU - Murashkina, Arina Valeryevna
AU - Kuliukhina, Daria Sergeevna
AU - Averin, Alexei Dmitrievich
AU - Abel, Anton Sergeevich
AU - Savelyev, Evgenii Nikolaevich
AU - Orlinson, Boris Semionovich
AU - Novakov, Ivan Aleksandrovich
AU - Correia, Carlos R.D.
AU - Beletskaya, Irina Petrovna
PY - 2022
DA - 2022/01/03
PB - Mendeleev Communications
SP - 91-93
IS - 1
VL - 32
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Murashkina,
author = {Arina Valeryevna Murashkina and Daria Sergeevna Kuliukhina and Alexei Dmitrievich Averin and Anton Sergeevich Abel and Evgenii Nikolaevich Savelyev and Boris Semionovich Orlinson and Ivan Aleksandrovich Novakov and Carlos R.D. Correia and Irina Petrovna Beletskaya},
title = {A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.029},
number = {1},
pages = {91--93},
doi = {10.1016/j.mencom.2022.01.029}
}
MLA
Cite this
MLA Copy
Murashkina, Arina Valeryevna, et al. “A comparison of homogeneous and heterogeneous copper catalyzed arylation of amines.” Mendeleev Communications, vol. 32, no. 1, Jan. 2022, pp. 91-93. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.029.

Keywords

amination
copper
heterogeneous catalysis
homogeneous catalysis
iodoarenes
nanoparticles

Abstract

Comparison of the homogeneous and heterogeneous copper-catalyzed arylation of model primary amines with (hetero)-aryl iodides in DMSO revealed a comparable efficiency of CuI and commercially available unsupported copper nanoparticles (25 nm size) in the presence of 2-isobutyryl-cyclohexanone or L-proline.

References

2.
Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development
Sambiagio C., Marsden S.P., Blacker A.J., McGowan P.C.
Chemical Society Reviews, 2014
5.
10.1016/j.mencom.2022.01.029_b0025
Shaughnessy
Copper-Catalyzed Amination of Aryl and Alkenyl Electrophiles, 2017
6.
10.1016/j.mencom.2022.01.029_b0030
Tang
Synthesis, 2008
8.
Copper-Catalyzed Suzuki Cross-Coupling Using Mixed Nanocluster Catalysts
Thathagar M.B., Beckers J., Rothenberg G.
Journal of the American Chemical Society, 2002
9.
Palladium-free and ligand-free Sonogashira cross-coupling
Thathagar M.B., Beckers J., Rothenberg G.
Green Chemistry, 2004
10.
The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations
Beletskaya I., Abel A., Averin A., Buryak A., Savelyev E., Orlinson B., Novakov I.
Synthesis, 2017
11.
Arylation of adamantanamines: IX. Copper(I)-catalyzed arylation of adamantane-containing amines
Averin A.D., Panchenko S.P., Abel A.S., Maloshitskaya O.A., Butov G.M., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Russian Journal of Organic Chemistry, 2017
12.
Hit-to-Lead studies: The discovery of potent adamantane amide P2X7 receptor antagonists
Baxter A., Bent J., Bowers K., Braddock M., Brough S., Fagura M., Lawson M., McInally T., Mortimore M., Robertson M., Weaver R., Webborn P.
Bioorganic and Medicinal Chemistry Letters, 2003
13.
2-Phenylimidazopyridines, a New Series of Golgi Compounds with Potent Antiviral Activity
Banie H., Sinha A., Thomas R.J., Sircar J.C., Richards M.L.
Journal of Medicinal Chemistry, 2007
14.
Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1
Tice C.M., Zhao W., Krosky P.M., Kruk B.A., Berbaum J., Johnson J.A., Bukhtiyarov Y., Panemangalore R., Scott B.B., Zhao Y., Bruno J.G., Howard L., Togias J., Ye Y., Singh S.B., et. al.
Bioorganic and Medicinal Chemistry Letters, 2010
15.
Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines
Lyakhovich M.S., Murashkina A.V., Averin A.D., Abel A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Beletskaya I.P.
Russian Journal of Organic Chemistry, 2019
16.
Arylation of Adamantanamines: XI. Comparison of the Catalytic Efficiency of Palladium and Copper Complexes in Reactions of Adamantanamines with Fluorinated 2-Bromopyridines
Lyakhovich M.S., Murashkina A.V., Panchenko S.P., Averin A.D., Abel A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Russian Journal of Organic Chemistry, 2021
17.
Abel A.S., Kharlamova A.D., Averin A.D., Beletskaya I.P.
Mendeleev Communications, 2021
18.
Recent achievements in copper catalysis for C-N bond formation
Averin A.D., Abel A.S., Grigorova O.K., Latyshev G.V., Kotovshchikov Y.N., Mitrofanov A.Y., Bessmertnykh-Lemeune A., Beletskaya I.P.
Pure and Applied Chemistry, 2020
19.
Rapid extraction of lead(II) from succinate media with n-octylaniline in toluene
SHILIMKAR T., ANUSE M.
Separation and Purification Technology, 2002
20.
Rapid extraction separation of aluminium(III) from associated elements with n-octylaniline from succinate media
Shilimkar T.N., Kolekar S.S., Anuse M.A.
Separation and Purification Technology, 2005
24.
Extraction of iridium(III) by ion-pair formation with 2-octylaminopyridine in weak organic acid media
Suryavanshi V.J., Patil M.M., Zanje S.B., Kokare A.N., Kore G.D., Anuse M.A., Mulik G.N.
Separation Science and Technology, 2016
25.
Development of liquid-liquid extraction and separation method for ruthenium(III) with 2-octylaminopyridine from succinate media: Analysis of catalysts
Suryavanshi V.J., Patil M.M., Zanje S.B., Kokare A.N., Gaikwad A.P., Anuse M.A., Mulik G.N.
Russian Journal of Inorganic Chemistry, 2017
26.
Liquid–liquid extraction of uranium(VI) from weak sodium acetate medium using 2-octylaminopyridine: real sample analysis
Kore G.D., Zanje S.B., Kokare A.N., Suryavanshi V.J., Anuse M.A., Kolekar S.S.
Journal of Radioanalytical and Nuclear Chemistry, 2021
27.
10.1016/j.mencom.2022.01.029_b0135
Wahyudi
Sci. Eng., 2018
28.
Enhanced catalytic performance by copper nanoparticle–graphene based composite
Mondal P., Sinha A., Salam N., Roy A.S., Jana N.R., Islam S.M.
RSC Advances, 2013
29.
Cu and Cu-Based Nanoparticles: Synthesis and Applications in Catalysis
Gawande M.B., Goswami A., Felpin F., Asefa T., Huang X., Silva R., Zou X., Zboril R., Varma R.S.
Chemical Reviews, 2016
30.
Formation of C-C, C-S and C-N bonds catalysed by supported copper nanoparticles
Mitrofanov A.Y., Murashkina A.V., Martín-García I., Alonso F., Beletskaya I.P.
Catalysis Science and Technology, 2017
31.
10.1016/j.mencom.2022.01.029_b0155
Esmaeilpour
Appl. Organomet. Chem., 2018