Copper Nanoparticles and Copper-Containing Metal-Organic Coordination Polymers in the Catalytic Aminayion of 2-Halopyridines

Dmitry A. Leksakov; Лексаков Дмитрий Александрович; Anastasia S. Borisova; Борисова Анастасия Сергеевна; Arina V. Murashkina; Мурашкина Арина Валерьевна; Daria S. Kulyukhina; Кулюхина Дарья Сергеевна; Alexey D. Averin; Аверин Алексей Дмитриевич; Vadim V. Vergun; Вергун Вадим Вячеславович; Vera I. Isaeva; Исаева Вера Ильинична; Evgeny N. Savelyev; Савельев Евгений Николаевич; Ivan A. Novakov; Новаков Иван Александрович; Irina P. Beletskaya; Белецкая Ирина Петровна

doi:10.31857/S0514749225040011

Copper Nanoparticles and Copper-Containing Metal-Organic Coordination Polymers in the Catalytic Aminayion of 2-Halopyridines

Autores: Leksakov D.A.¹, Borisova A.S.¹, Murashkina A.V.¹, Kulyukhina D.S.¹, Averin A.D.¹^,2, Vergun V.V.³, Isaeva V.I.³, Savelyev E.N.⁴, Novakov I.A.⁴, Beletskaya I.P.¹^,2
Afiliações:
1. Lomonosov Moscow State University
2. Frumkin Institute of Physical Chemistry and Electrochemistry of the RAS
3. Zelinsky Institute of Organic Chemistry of the RAS
4. Volgograd State Technical University
Edição: Volume 61, Nº 4 (2025)
Páginas: 353-363
Seção: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://consilium.orscience.ru/0514-7492/article/view/689608
DOI: https://doi.org/10.31857/S0514749225040011
EDN: https://elibrary.ru/SDDCKV
ID: 689608

Citar

Texto integral

Acesso aberto
Acesso é fechado

Acesso está concedido
Acesso é fechado

Acesso é pago ou somente para assinantes

Resumo
Texto integral
Sobre autores
Bibliografia
Arquivos suplementares
Estatísticas

Resumo

The efficiency of copper-containing metal-organic coordination polymers (Cu-MOFs) and commercially available non-immobilized copper nanoparticles (CuNPs) in the amination of 2-iodopyridine, 2-bromo-pyridine and its trifluoromethyl derivatives with n-octylamine and adamantane-containing amines with different steric hindrances at the amino group was compared. The yields of the amination products under optimized conditions were shown to be close for both catalytic systems. To achieve good yields in the case of 2-bromopyridine, an increase in the concentration of reagents and the use of 2 equiv. of haloarene are required, while the introduction of a trifluoromethyl group at position 6 of the pyridine ring improves the yields of the amination products. Increasing steric hindrances at the amino group leads to a noticeable decrease in the yields of products in the Cu-MOF catalyzed reactions. However, the use of CuNPs allows for successful reactions with such amines, and CuNPs of 25 nm average size demonstrated an advantage over bifractional nanoparticles of 10/80 nm. On the other hand, increasing the concentration of reagents in the Cu-MOF catalyzed reactions provides good yields of the target compounds without addition ligands.

Palavras-chave

amination, pyridine, haloarenes, amines, adamantane, copper nanoparticles, metal-organic coordination polymers

Texto integral

Bibliografia

Chui S.S.-Y., Lo S.M.-F., Charmant J.P.H., Orpen A.G., Williams I.D. Science. 1999, 283, 1148–1150. doi: 10.1126/science.283.5405.1148
Tian T., Zeng Z., Vulpe D., Casco M.E., Divitini G., Midgley P.A., Silvestre-Albero J., Tan J.C., Moghadam P.Z., Fairen-Jimenez D. Nat. Mater. 2018, 17, 174–179. doi: 10.1038/nmat5050
Mu X., Chen Y., Lester E., Wu T. Microporous Mesoporous Mater. 2018, 270, 249–257. doi: 10.1016/j.micromeso.2018.05.027
Mahmoud E., Ali L., El Sayah A., Alkhatib S.A., Abdulsalam H., Juma M., Al-Muhtaseb A.H. Crystals. 2019, 9, 406. doi: 10.3390/cryst9080406
Yepez R., Garcia S., Schachat P., Sanchez-Sanchez M., Gonzaґlez-Estefan J.H., Gonzalez-Zamora E., Ibarra I.A., Aguilar-Pliego J. New J. Chem. 2015, 39, 5112–5115. doi: 10.1039/C5NJ00247H
Liu Y., Wang S., Wu X., Zhao Y., Lu Y., Zhang Y., Xu G., Zhang J., Guo Z., Chen X. Microporous Mesoporous Mater. 2019, 279, 228–233. doi: 10.1016/j.micromeso.2018.12.039
Ганина О.Г., Бондаренко Г.Н., Исаева В.И., Кус-тов Л.М., Белецкая И.П. ЖОрХ 2019, 55, 1813–1820. [Ganina O.G., Bondarenko G.N., Isaeva V.I., Kustov L.M., Beletskaya I.P. Russ. J. Org. Chem. 2019, 55, 1813–1820.] doi: 10.1134/S1070428019120017
Han S., Ciufo R.A., Wygant B.R., Keitz B.K., Mullins C.B. ACS Catal. 2020, 10, 4997–5007. doi: 10.1021/acscatal.0c00592
Fan S., Dong W., Huang X., Gao H., Wang J., Jin Z., Tang J., Wang G. ACS Catal. 2017, 7, 243–249. doi: 10.1021/acscatal.6b02614
Llabrés i Xamena F.X., Casanova O., Tailleur R.G., Garcia H., Corma A. J. Catal. 2008, 255, 220–227. doi: 10.1016/j.jcat.2008.02.011
Luz I., Leon A., Boronat M., Llabres i Xamena F.X., Corma A. Catal. Sci. Technol. 2013, 3, 371–379. doi: 10.1039/C2CY20449E
Qi Y., Luan Y., Yu J., Peng X., Wang G. Chem. Eur. J. 2015, 21, 1589–1597. doi: 10.1002/chem.201405685
Kargar P.G., Aryanejad S., Bagherzade G. Appl. Organomet. Chem. 2020, 34, e5965. doi: 10.1002/aoc.5965
Cai J., Zhuang Y., Chen Y., Xiao L., Zhao Y., Jiang X., Hou L., Li Z. ChemCatChem. 2020, 12, 6241–6247. doi: 10.1002/cctc.202001140
Singh R., Singh G., George N., Singh G., Gupta S., Singh H., Kaur G., Singh J. Catalysts. 2023, 13, 130. doi: 10.3390/catal13010130
Zhang X., Qin J., Ma R., Shi L. J. Chem. Res. 2021, 45, 795–799. doi: 10.1177/17475198211026506
Борисова А.С., Кулюхина Д.С., Малышева А.С., Мурашкина А.В., Аверин А.Д., Вергун В.В., Исае-ва В.И., Савельев Е.Н., Новаков И.А., Белецкая И.П. Изв. АН сер. хим. 2024, 73, 3567–3577.
Murashkina A.V., Kuliukhina D.S., Averin A.D., Abel A.S., Savelyev E.N., Orlinson B.S., Novakov I.A., Correia C.R.D., Beletskaya I.P. Mendeleev Commun. 2022, 32, 91–93. doi: 10.1016/j.mencom.2022.01.029
Murashkina A.V., Averin A.D., Panchenko, S.P., Abel, A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Correia C.R.D., Beletskaya I.P. Russ. J. Org. Chem. 2022, 58, 15–24. doi: 10.1134/S107042802201002X
Fomenko V.I., Murashkina A.V., Averin A.D., Shesterkina A.A., Beletskaya I.P. Catalysts. 2023, 13, 331. doi: 10.3390/catal13020331
Морозов И.С., Петров В.И., Сергеева С.А. Фарма-кология адамантанов. Волгоградская медицинская академия, 2001. 320 с.
Novakov I.A., Orlinson B.S., Savelyev E.N., Potaenkova E.A., Shilin A.K. Patent RF RU 2495020 C1 2013.
Gopalan B., Thomas A., Shah D.M. PCT Int. Appl. WO 2006090244 2006; Chem. Abstr. 2006, 145, 292604.
Averin A.D., Ranyuk E.R., Golub S.L., Buryak A.K., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P. Synthesis. 2007, 2007, 2215–2221. doi: 10.1055/s-2007-983760
Isaeva V.I., Saifutdinov B.R., Chernyshev V.V., Vergun V.V., Kapustin G.I., Kurnysheva Y.P., Ilyin M.M., Kustov L.M. Molecules 2020, 25, 2648. doi: 10.3390/molecules25112648
Gedye R.N., Bozic J., Durbano P.M., Williamson B. Talanta 1989, 36, 1055–1058. doi: 10.1016/0039-9140(89)80194-8
Abel A.S., Averin A.D., Anokhin M.V., Maloshitskaya O.A., Butov G.M., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P. Russ. J. Org. Chem. 2015, 51, 301–308. doi: 10.1134/S1070428015030021
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. Russ. J. Org. Chem. 2021, 57, 768–783. doi: 10.1134/S1070428021050031
Lyakhovich M.S., Murashkina A.V., Averin A.D., Abel A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Beletskaya I.P. Russ. J. Org. Chem. 2019, 55, 737–747. doi: 10.1134/S1070428019060010
Phan N.T.S., Nguyen T.T., Nguyen K.D., Vo A.X.T. Appl. Catal. A 2013, 464-465, 128–135. doi: 10.1016/j.apcata.2013.05.034.