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Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids. / Titov, Gleb D. ; Antonychev, Grigory I. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. ; Rogacheva, Elizaveta V. ; Kraeva, Liudmila A. ; Rostovskii, Nikolai V. .

в: Organic Letters, Том 25, № 15, 06.04.2023, стр. 2707−2712.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Titov, GD, Antonychev, GI, Novikov, MS, Khlebnikov, AF, Rogacheva, EV, Kraeva, LA & Rostovskii, NV 2023, 'Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids', Organic Letters, Том. 25, № 15, стр. 2707−2712.

APA

Titov, G. D., Antonychev, G. I., Novikov, M. S., Khlebnikov, A. F., Rogacheva, E. V., Kraeva, L. A., & Rostovskii, N. V. (2023). Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids. Organic Letters, 25(15), 2707−2712.

Vancouver

Titov GD, Antonychev GI, Novikov MS, Khlebnikov AF, Rogacheva EV, Kraeva LA и пр. Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids. Organic Letters. 2023 Апр. 6;25(15):2707−2712.

Author

Titov, Gleb D. ; Antonychev, Grigory I. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. ; Rogacheva, Elizaveta V. ; Kraeva, Liudmila A. ; Rostovskii, Nikolai V. . / Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids. в: Organic Letters. 2023 ; Том 25, № 15. стр. 2707−2712.

BibTeX

@article{384235a08daa428dafe841330af880f9,
title = "Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids",
abstract = "An orthogonal reactivity of diazo compounds toward azirine-2-carboxylic acids, switching with the reaction conditions, is demonstrated. A gold-catalyzed reaction is N selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O−H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metalbound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.",
author = "Titov, {Gleb D.} and Antonychev, {Grigory I.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.} and Rogacheva, {Elizaveta V.} and Kraeva, {Liudmila A.} and Rostovskii, {Nikolai V.}",
year = "2023",
month = apr,
day = "6",
language = "English",
volume = "25",
pages = "2707−2712",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "15",

}

RIS

TY - JOUR

T1 - Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H‑Azirine-2-carboxylic Acids

AU - Titov, Gleb D.

AU - Antonychev, Grigory I.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

AU - Rogacheva, Elizaveta V.

AU - Kraeva, Liudmila A.

AU - Rostovskii, Nikolai V.

PY - 2023/4/6

Y1 - 2023/4/6

N2 - An orthogonal reactivity of diazo compounds toward azirine-2-carboxylic acids, switching with the reaction conditions, is demonstrated. A gold-catalyzed reaction is N selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O−H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metalbound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.

AB - An orthogonal reactivity of diazo compounds toward azirine-2-carboxylic acids, switching with the reaction conditions, is demonstrated. A gold-catalyzed reaction is N selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O−H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metalbound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.

UR - https://www.sciencedirect.com/org/science/article/abs/pii/S152370602300528X

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c00823

M3 - Article

VL - 25

SP - 2707−2712

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 15

ER -

ID: 105363083