Organic Letters, volume 23, issue 20, pages 8045-8049
Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines
Publication type: Journal Article
Publication date: 2021-10-01
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A high-yield method for the introduction of a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives by the direct cross-coupling with 2-(trialkylstannyl)pyridines has been described. The reaction works well with 3-, 4-, or 5-substituted 2-stannylpyridines and can be also employed for the synthesis of 2-(thiazol-2-yl)-2H-azirines. According to DFT calculations, the reaction proceeds through the sequence of SN2'-substitution of bromine, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring.
Citations by journals
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1
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Organic Chemistry Frontiers
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Organic Chemistry Frontiers
1 publication, 25%
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Organic Letters
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Organic Letters
1 publication, 25%
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
1 publication, 25%
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Russian Journal of Organic Chemistry
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Russian Journal of Organic Chemistry
1 publication, 25%
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1
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Citations by publishers
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1
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 25%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 25%
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Wiley
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Wiley
1 publication, 25%
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Pleiades Publishing
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Pleiades Publishing
1 publication, 25%
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1
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Agafonova A. V. et al. Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines // Organic Letters. 2021. Vol. 23. No. 20. pp. 8045-8049.
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Agafonova A. V., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines // Organic Letters. 2021. Vol. 23. No. 20. pp. 8045-8049.
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TY - JOUR
DO - 10.1021/acs.orglett.1c03060
UR - https://doi.org/10.1021%2Facs.orglett.1c03060
TI - Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines
T2 - Organic Letters
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
AU - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
PY - 2021
DA - 2021/10/01 00:00:00
PB - American Chemical Society (ACS)
SP - 8045-8049
IS - 20
VL - 23
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2021_Agafonova,
author = {Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov and Anastasiya V Agafonova and Ilia A Smetanin},
title = {Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021%2Facs.orglett.1c03060},
number = {20},
pages = {8045--8049},
doi = {10.1021/acs.orglett.1c03060}
}
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MLA
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Agafonova, Anastasiya V., et al. “Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines.” Organic Letters, vol. 23, no. 20, Oct. 2021, pp. 8045-8049. https://doi.org/10.1021%2Facs.orglett.1c03060.