Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes
Pavel A. Volkov
1, 2, 3, 4, 5
,
Anton A Telezhkin
1, 2, 3, 4, 5
,
Kseniya O Khrapova
1, 2, 3, 4, 5
,
Nina I. Ivanova
1, 2, 3, 4, 5
,
Alexander I Albanov
1, 2, 3, 4, 5
,
Nina K Gusarova
1, 2, 3, 4, 5
,
B. A. Trofimov
1, 2, 3, 4, 5
3
Siberian branch of the Russian Academy of sciences
4
664033 Irkutsk
|
5
RUSSIAN FEDERATION
|
Publication type: Journal Article
Publication date: 2021-02-26
scimago Q2
wos Q3
SJR: 0.493
CiteScore: 5.0
Impact factor: 2.5
ISSN: 11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Abstract
Terminal acylacetylenes, typical electron-deficient acetylenes, drive SHN cross-coupling of pyridines with secondary phosphine chalcogenides under metal-free mild conditions (20–75 °C) to afford 4-chalcogenophosphorylpyridines in up to 70% yield. The reaction proceeds via 2,4-migration of chalcogenophosphoryl groups in the intermediate 1-acylvinyl-2-phosphoryl dihydropyridines with simultaneous redox elimination of the vinyl ketone oligomers. These results are generalized in a concept of trimodal (polarization/deprotonation/oxidation) catalyst-like assistance of electron-deficient acetylenes in SHN reaction of the pyridinoid heterocycles with PH-nucleophiles, which comprises: (i) repolarization (umpolung) of the pyridine ring, (ii) deprotonation of secondary phosphine chalcogenides to generate phosphorus-centered anions and (iii) oxidation of the dihydro intermediates.
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Total citations:
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Citations from 2024:
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(18.18%)
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Volkov P. A. et al. Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes // New Journal of Chemistry. 2021. Vol. 45. No. 14. pp. 6206-6219.
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Volkov P. A., Telezhkin A. A., Khrapova K. O., Ivanova N. I., Albanov A. I., Gusarova N. K., Trofimov B. A. Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes // New Journal of Chemistry. 2021. Vol. 45. No. 14. pp. 6206-6219.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/d1nj00245g
UR - https://xlink.rsc.org/?DOI=D1NJ00245G
TI - Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes
T2 - New Journal of Chemistry
AU - Volkov, Pavel A.
AU - Telezhkin, Anton A
AU - Khrapova, Kseniya O
AU - Ivanova, Nina I.
AU - Albanov, Alexander I
AU - Gusarova, Nina K
AU - Trofimov, B. A.
PY - 2021
DA - 2021/02/26
PB - Royal Society of Chemistry (RSC)
SP - 6206-6219
IS - 14
VL - 45
SN - 1144-0546
SN - 1369-9261
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Volkov,
author = {Pavel A. Volkov and Anton A Telezhkin and Kseniya O Khrapova and Nina I. Ivanova and Alexander I Albanov and Nina K Gusarova and B. A. Trofimov},
title = {Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes},
journal = {New Journal of Chemistry},
year = {2021},
volume = {45},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://xlink.rsc.org/?DOI=D1NJ00245G},
number = {14},
pages = {6206--6219},
doi = {10.1039/d1nj00245g}
}
Cite this
MLA
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Volkov, Pavel A., et al. “Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes.” New Journal of Chemistry, vol. 45, no. 14, Feb. 2021, pp. 6206-6219. https://xlink.rsc.org/?DOI=D1NJ00245G.
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