Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds
Publication type: Journal Article
Publication date: 2021-09-13
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
The reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals is disclosed. Traditionally, these substrates have been considered as reactants for ionic transformations. Highly selective and efficient N-oxyl radical mediated C–O coupling of substituted barbituric or Meldrum’s acids with N-hydroxy compounds (N-hydroxyimides, hydroxamic acids, oximes, and N-hydroxybenzotriazole) was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C–O coupling was demonstrated using diacetyliminoxyl as both the oxidant (hydrogen-atom acceptor) and the coupling partner.
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Total citations:
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Citations from 2024:
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(25%)
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Terent’ev A. O. et al. Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds // Synthesis. 2021. Vol. 54. No. 02. pp. 506-516.
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Terent’ev A. O., Krylov I. B., Krylov I. B., Paveliev S. A., Budnikov A. S., Segida O. O., Merkulova V. M., Vil’ V. A., Nikishin G. I. Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds // Synthesis. 2021. Vol. 54. No. 02. pp. 506-516.
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RIS
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TY - JOUR
DO - 10.1055/a-1643-7642
UR - https://doi.org/10.1055/a-1643-7642
TI - Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds
T2 - Synthesis
AU - Terent’ev, Alexander O.
AU - Krylov, Igor B.
AU - Krylov, Igor B
AU - Paveliev, Stanislav A
AU - Budnikov, Alexander S
AU - Segida, Oleg O
AU - Merkulova, Valentina M
AU - Vil’, Vera A.
AU - Nikishin, Gennady I.
PY - 2021
DA - 2021/09/13
PB - Georg Thieme Verlag KG
SP - 506-516
IS - 02
VL - 54
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2021_Terent’ev,
author = {Alexander O. Terent’ev and Igor B. Krylov and Igor B Krylov and Stanislav A Paveliev and Alexander S Budnikov and Oleg O Segida and Valentina M Merkulova and Vera A. Vil’ and Gennady I. Nikishin},
title = {Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds},
journal = {Synthesis},
year = {2021},
volume = {54},
publisher = {Georg Thieme Verlag KG},
month = {sep},
url = {https://doi.org/10.1055/a-1643-7642},
number = {02},
pages = {506--516},
doi = {10.1055/a-1643-7642}
}
Cite this
MLA
Copy
Terent’ev, Alexander O., et al. “Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds.” Synthesis, vol. 54, no. 02, Sep. 2021, pp. 506-516. https://doi.org/10.1055/a-1643-7642.