Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids
Тип публикации: Journal Article
Дата публикации: 2023-04-06
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
37023109
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
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 metal-bound 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.
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Titov G. D. et al. Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids // Organic Letters. 2023. Vol. 25. No. 15. pp. 2707-2712.
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Titov G. D., Antonychev G. I., Novikov M. S., Khlebnikov A. F., Rogacheva E. V., Kraeva L. A., Kraeva L. A., Rostovskii N. V. Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids // Organic Letters. 2023. Vol. 25. No. 15. pp. 2707-2712.
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TY - JOUR
DO - 10.1021/acs.orglett.3c00823
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c00823
TI - Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids
T2 - Organic Letters
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 - Kraeva, Ludmila A
AU - Rostovskii, Nikolai V
PY - 2023
DA - 2023/04/06
PB - American Chemical Society (ACS)
SP - 2707-2712
IS - 15
VL - 25
PMID - 37023109
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2023_Titov,
author = {Gleb D Titov and Grigory I. Antonychev and Mikhail S. Novikov and Alexander F Khlebnikov and Elizaveta V Rogacheva and Liudmila A Kraeva and Ludmila A Kraeva and Nikolai V Rostovskii},
title = {Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c00823},
number = {15},
pages = {2707--2712},
doi = {10.1021/acs.orglett.3c00823}
}
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MLA
Скопировать
Titov, Gleb D., et al. “Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids.” Organic Letters, vol. 25, no. 15, Apr. 2023, pp. 2707-2712. https://pubs.acs.org/doi/10.1021/acs.orglett.3c00823.