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XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines. / Агафонова, Анастасия Викторовна; Павленко, Юлия Игоревна; Занахов, Тимур Олегович; Хлебников, Александр Феодосиевич; Новиков, Михаил Сергеевич.

In: Organic Letters, Vol. 27, No. 45, 04.11.2025, p. 12634-12638.

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

Harvard

Агафонова, АВ, Павленко, ЮИ, Занахов, ТО, Хлебников, АФ & Новиков, МС 2025, 'XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines', Organic Letters, vol. 27, no. 45, pp. 12634-12638. https://doi.org/10.1021/acs.orglett.5c04084

APA

Агафонова, А. В., Павленко, Ю. И., Занахов, Т. О., Хлебников, А. Ф., & Новиков, М. С. (2025). XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines. Organic Letters, 27(45), 12634-12638. https://doi.org/10.1021/acs.orglett.5c04084

Vancouver

Агафонова АВ, Павленко ЮИ, Занахов ТО, Хлебников АФ, Новиков МС. XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines. Organic Letters. 2025 Nov 4;27(45):12634-12638. https://doi.org/10.1021/acs.orglett.5c04084

Author

Агафонова, Анастасия Викторовна ; Павленко, Юлия Игоревна ; Занахов, Тимур Олегович ; Хлебников, Александр Феодосиевич ; Новиков, Михаил Сергеевич. / XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines. In: Organic Letters. 2025 ; Vol. 27, No. 45. pp. 12634-12638.

BibTeX

@article{24b0d8367d1b4dc8a5495f800cf3a815,
title = "XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines",
abstract = "We report a radical strategy for direct C2-alkylation of 2H-azirines via generation of elusive 2H-azirinyl radicals. These highly reactive intermediates are accessed under mild halogen-atom transfer conditions from readily available 2-haloazirines. The resulting cyclic radicals undergo regioselective Giese-type additions to electron-deficient alkenes, retaining the azirine ring. Mechanistic studies, including spin-trapping and DFT analysis, support a free radical pathway. The adducts undergo base-promoted ring expansion to yield 6-aminopyridines, underscoring this platform's synthetic utility.",
author = "Агафонова, {Анастасия Викторовна} and Павленко, {Юлия Игоревна} and Занахов, {Тимур Олегович} and Хлебников, {Александр Феодосиевич} and Новиков, {Михаил Сергеевич}",
year = "2025",
month = nov,
day = "4",
doi = "10.1021/acs.orglett.5c04084",
language = "English",
volume = "27",
pages = "12634--12638",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "45",

}

RIS

TY - JOUR

T1 - XAT-Generated Azirinyl Radicals in Selective Giese-Type Alkylation of 2H-Azirines

AU - Агафонова, Анастасия Викторовна

AU - Павленко, Юлия Игоревна

AU - Занахов, Тимур Олегович

AU - Хлебников, Александр Феодосиевич

AU - Новиков, Михаил Сергеевич

PY - 2025/11/4

Y1 - 2025/11/4

N2 - We report a radical strategy for direct C2-alkylation of 2H-azirines via generation of elusive 2H-azirinyl radicals. These highly reactive intermediates are accessed under mild halogen-atom transfer conditions from readily available 2-haloazirines. The resulting cyclic radicals undergo regioselective Giese-type additions to electron-deficient alkenes, retaining the azirine ring. Mechanistic studies, including spin-trapping and DFT analysis, support a free radical pathway. The adducts undergo base-promoted ring expansion to yield 6-aminopyridines, underscoring this platform's synthetic utility.

AB - We report a radical strategy for direct C2-alkylation of 2H-azirines via generation of elusive 2H-azirinyl radicals. These highly reactive intermediates are accessed under mild halogen-atom transfer conditions from readily available 2-haloazirines. The resulting cyclic radicals undergo regioselective Giese-type additions to electron-deficient alkenes, retaining the azirine ring. Mechanistic studies, including spin-trapping and DFT analysis, support a free radical pathway. The adducts undergo base-promoted ring expansion to yield 6-aminopyridines, underscoring this platform's synthetic utility.

UR - https://www.mendeley.com/catalogue/762c0d61-c693-3093-b6ec-3e14ee13899f/

U2 - 10.1021/acs.orglett.5c04084

DO - 10.1021/acs.orglett.5c04084

M3 - Article

VL - 27

SP - 12634

EP - 12638

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 45

ER -

ID: 143421381