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
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34597057
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.
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Total citations:
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Citations from 2024:
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(71%)
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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://pubs.acs.org/doi/10.1021/acs.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 - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2021
DA - 2021/10/01
PB - American Chemical Society (ACS)
SP - 8045-8049
IS - 20
VL - 23
PMID - 34597057
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2021_Agafonova,
author = {Anastasiya V Agafonova and Ilia A Smetanin and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
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://pubs.acs.org/doi/10.1021/acs.orglett.1c03060},
number = {20},
pages = {8045--8049},
doi = {10.1021/acs.orglett.1c03060}
}
Cite this
MLA
Copy
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://pubs.acs.org/doi/10.1021/acs.orglett.1c03060.