Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates
Тип публикации: Journal Article
Дата публикации: 2022-10-27
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36302230
Organic Chemistry
Краткое описание
A diazo strategy for the intramolecular azirine ring expansion was developed. Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates under Rh catalysis in the presence of water. According to DFT calculations, the formation of only pyrrolinone derivatives and the absence of O-H insertion products of Rh carbene into water are due to the low Gibbs free energy of the transition state for the concerted opening of the azirine ring and recyclization to pyrrolone in intermediate Rh complexes.
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Zanakhov T. O. et al. Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates // Journal of Organic Chemistry. 2022. Vol. 87. No. 22. pp. 15598-15607.
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Zanakhov T. O., Galenko E. E., Novikov M. S., Khlebnikov A. F. Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates // Journal of Organic Chemistry. 2022. Vol. 87. No. 22. pp. 15598-15607.
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TY - JOUR
DO - 10.1021/acs.joc.2c02177
UR - https://pubs.acs.org/doi/10.1021/acs.joc.2c02177
TI - Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates
T2 - Journal of Organic Chemistry
AU - Zanakhov, Timur O
AU - Galenko, Ekaterina E
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2022
DA - 2022/10/27
PB - American Chemical Society (ACS)
SP - 15598-15607
IS - 22
VL - 87
PMID - 36302230
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2022_Zanakhov,
author = {Timur O Zanakhov and Ekaterina E Galenko and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.2c02177},
number = {22},
pages = {15598--15607},
doi = {10.1021/acs.joc.2c02177}
}
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Zanakhov, Timur O., et al. “Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1 H-pyrrole-2-carboxylates.” Journal of Organic Chemistry, vol. 87, no. 22, Oct. 2022, pp. 15598-15607. https://pubs.acs.org/doi/10.1021/acs.joc.2c02177.
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