Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Sofya I Scherbinina
1, 2
,
Oleg V. Fedorov
1
,
Vitalij V Levin
1
,
Vladimir A. Kokorekin
1, 3
,
Marina I. Struchkova
1
,
1
Publication type: Journal Article
Publication date: 2017-11-30
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29172505
Organic Chemistry
Abstract
A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.
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Total citations:
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Citations from 2024:
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GOST
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Scherbinina S. I. et al. Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers // Journal of Organic Chemistry. 2017. Vol. 82. No. 24. pp. 12967-12974.
GOST all authors (up to 50)
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Scherbinina S. I., Fedorov O. V., Levin V. V., Kokorekin V. A., Struchkova M. I., Dilman A. D. Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers // Journal of Organic Chemistry. 2017. Vol. 82. No. 24. pp. 12967-12974.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.7b02467
UR - https://doi.org/10.1021/acs.joc.7b02467
TI - Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
T2 - Journal of Organic Chemistry
AU - Scherbinina, Sofya I
AU - Fedorov, Oleg V.
AU - Levin, Vitalij V
AU - Kokorekin, Vladimir A.
AU - Struchkova, Marina I.
AU - Dilman, Alexander D
PY - 2017
DA - 2017/11/30
PB - American Chemical Society (ACS)
SP - 12967-12974
IS - 24
VL - 82
PMID - 29172505
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Scherbinina,
author = {Sofya I Scherbinina and Oleg V. Fedorov and Vitalij V Levin and Vladimir A. Kokorekin and Marina I. Struchkova and Alexander D Dilman},
title = {Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.7b02467},
number = {24},
pages = {12967--12974},
doi = {10.1021/acs.joc.7b02467}
}
Cite this
MLA
Copy
Scherbinina, Sofya I., et al. “Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers.” Journal of Organic Chemistry, vol. 82, no. 24, Nov. 2017, pp. 12967-12974. https://doi.org/10.1021/acs.joc.7b02467.
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