Standard

Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls. / Gulman, M.M.; Polienko, Yu.F.; Trakhinina, S.Yu. et al.

In: Chemistry for Sustainable Development, Vol. 33, No. 5, 4, 2025, p. 510-519.

Research output: Contribution to journal › Article › peer-review

Harvard

Gulman, MM, Polienko, YF, Trakhinina, SY, Gatilov, YV, Dobrynin, SA & Kirilyuk, IA 2025, 'Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls', Chemistry for Sustainable Development, vol. 33, no. 5, 4, pp. 510-519. https://doi.org/10.15372/csd2025684

APA

Gulman, M. M., Polienko, Y. F., Trakhinina, S. Y., Gatilov, Y. V., Dobrynin, S. A., & Kirilyuk, I. A. (2025). Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls. Chemistry for Sustainable Development, 33(5), 510-519. [4]. https://doi.org/10.15372/csd2025684

Vancouver

Gulman MM, Polienko YF, Trakhinina SY, Gatilov YV, Dobrynin SA, Kirilyuk IA. Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls. Chemistry for Sustainable Development. 2025;33(5):510-519. 4. doi: 10.15372/csd2025684

Author

Gulman, M.M. ; Polienko, Yu.F. ; Trakhinina, S.Yu. et al. / Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls. In: Chemistry for Sustainable Development. 2025 ; Vol. 33, No. 5. pp. 510-519.

BibTeX

@article{8d93ba5cf9c64a20a9b431f18fb64e49,
title = "Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls",
abstract = "The reaction of 2-R-5,5-diethyl-2-ethynylpyrrolidin-1-oxyls (where R = Et, i-Pr) with esters of azidoacetic and p-azidobenzoic acids in the presence of copper(I) salts has been studied. It was found that the presence of the bulky isopropyl substituent prevents the reaction with ethyl ether of p-azidobenzoic acid and decreases the yield of the corresponding triazole in the reaction with methyl ester of azidoacetic acid. The resulting nitroxides demonstrated a high degree of resistance to reduction by ascorbic acid, which was comparable to the stability of 3,4-bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidin-1-oxyl.",
keywords = "НИТРОКСИЛЬНЫЙ РАДИКАЛ, АЦЕТИЛЕНЫ, РЕАКЦИЯ АЗИД-АЛКИНОВОГО ЦИКЛОПРИСОЕДИНЕНИЯ, NITROXIDE, ACETYLENES, COPPER-CATALYSED AZIDE-ALKYNE CYCLOADDITION",
author = "M.M. Gulman and Yu.F. Polienko and S.Yu. Trakhinina and Yu.V. Gatilov and S.A. Dobrynin and I.A. Kirilyuk",
note = " Gulman M. M., Polienko Yu. F., Trakhinina S. Yu., Gatilov Yu. V., Dobrynin S. A., Kirilyuk I. A., Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls // Chemistry for Sustainable Development. - 2025. - Vol. 33. - No. 5. - P. 511–519. DOI: 10.15372/CSD2025684. EDN: FCTDEL. Funding: the work was supported by the Russian Science Foundation within Project No. 23-13-00178, https://rscf.ru/project/23-13-00178/.",
year = "2025",
doi = "10.15372/csd2025684",
language = "English",
volume = "33",
pages = "510--519",
journal = "Chemistry for Sustainable Development",
issn = "1817-1818",
publisher = "ФГУП {"}Издательство СО РАН{"}",
number = "5",

}

RIS

TY - JOUR

T1 - Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls

AU - Gulman, M.M.

AU - Polienko, Yu.F.

AU - Trakhinina, S.Yu.

AU - Gatilov, Yu.V.

AU - Dobrynin, S.A.

AU - Kirilyuk, I.A.

N1 - Gulman M. M., Polienko Yu. F., Trakhinina S. Yu., Gatilov Yu. V., Dobrynin S. A., Kirilyuk I. A., Copper-catalysed azide-alkyne cycloaddition of sterically shielded 2-ethynylpyrrolidin-1-oxyls // Chemistry for Sustainable Development. - 2025. - Vol. 33. - No. 5. - P. 511–519. DOI: 10.15372/CSD2025684. EDN: FCTDEL. Funding: the work was supported by the Russian Science Foundation within Project No. 23-13-00178, https://rscf.ru/project/23-13-00178/.

PY - 2025

Y1 - 2025

N2 - The reaction of 2-R-5,5-diethyl-2-ethynylpyrrolidin-1-oxyls (where R = Et, i-Pr) with esters of azidoacetic and p-azidobenzoic acids in the presence of copper(I) salts has been studied. It was found that the presence of the bulky isopropyl substituent prevents the reaction with ethyl ether of p-azidobenzoic acid and decreases the yield of the corresponding triazole in the reaction with methyl ester of azidoacetic acid. The resulting nitroxides demonstrated a high degree of resistance to reduction by ascorbic acid, which was comparable to the stability of 3,4-bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidin-1-oxyl.

AB - The reaction of 2-R-5,5-diethyl-2-ethynylpyrrolidin-1-oxyls (where R = Et, i-Pr) with esters of azidoacetic and p-azidobenzoic acids in the presence of copper(I) salts has been studied. It was found that the presence of the bulky isopropyl substituent prevents the reaction with ethyl ether of p-azidobenzoic acid and decreases the yield of the corresponding triazole in the reaction with methyl ester of azidoacetic acid. The resulting nitroxides demonstrated a high degree of resistance to reduction by ascorbic acid, which was comparable to the stability of 3,4-bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidin-1-oxyl.

KW - НИТРОКСИЛЬНЫЙ РАДИКАЛ

KW - АЦЕТИЛЕНЫ

KW - РЕАКЦИЯ АЗИД-АЛКИНОВОГО ЦИКЛОПРИСОЕДИНЕНИЯ

KW - NITROXIDE

KW - ACETYLENES

KW - COPPER-CATALYSED AZIDE-ALKYNE CYCLOADDITION

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001677410900001

UR - https://www.elibrary.ru/item.asp?id=88834904

UR - https://www.mendeley.com/catalogue/3b640bec-4c53-3632-aabe-13d3a0655315/

U2 - 10.15372/csd2025684

DO - 10.15372/csd2025684

M3 - Article

VL - 33

SP - 510

EP - 519

JO - Chemistry for Sustainable Development

JF - Chemistry for Sustainable Development

SN - 1817-1818

IS - 5

M1 - 4

ER -

ID: 83270345