Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans
Publication type: Journal Article
Publication date: 2020-09-21
scimago Q1
wos Q1
SJR: 3.782
CiteScore: 19.5
Impact factor: 13.1
ISSN: 21555435
General Chemistry
Catalysis
Abstract
An efficient strategy was developed for directing-group-free C–H functionalization of biomass-derived C6 furanic building block. Palladium-catalyzed C–H functionalization of the low-reactive C3 position was successfully performed in 2,5-diformylfuran, an important derivative of the biobased platform chemical 5-(hydroxymethyl)furfural. The ligand-free catalytic arylation was carried out without using protecting or directing groups, which is of key importance for the studied area to achieve waste-minimized and step-economic biomass processing. The experimental results combined with density functional theory calculations revealed a reaction mechanism and indicated that the presence of the aldehyde group is essential for catalytic reaction. Enolization of the aldehyde group and Pd binding play an important role in governing the overall C–H functionalization pathway. One of the obtained arylated furanic compounds was tested as a model substrate for reduction and oxidation of carbonyl groups to highlight its versatile synthetic potential.
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20
Total citations:
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Citations from 2024:
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(30%)
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Karlinskii B. Ya. et al. Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans // ACS Catalysis. 2020. Vol. 10. No. 19. pp. 11466-11480.
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Karlinskii B. Ya., Kostyukovich A. Y., Kucherov F. A., Galkin K. I., Kozlov K. S., Ananikov V. P. Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans // ACS Catalysis. 2020. Vol. 10. No. 19. pp. 11466-11480.
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RIS
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TY - JOUR
DO - 10.1021/acscatal.0c02143
UR - https://doi.org/10.1021/acscatal.0c02143
TI - Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans
T2 - ACS Catalysis
AU - Karlinskii, Bogdan Ya
AU - Kostyukovich, Alexander Yu.
AU - Kucherov, Fedor A
AU - Galkin, Konstantin I
AU - Kozlov, Kirill S.
AU - Ananikov, Valentine P.
PY - 2020
DA - 2020/09/21
PB - American Chemical Society (ACS)
SP - 11466-11480
IS - 19
VL - 10
SN - 2155-5435
ER -
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BibTex (up to 50 authors)
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@article{2020_Karlinskii,
author = {Bogdan Ya Karlinskii and Alexander Yu. Kostyukovich and Fedor A Kucherov and Konstantin I Galkin and Kirill S. Kozlov and Valentine P. Ananikov},
title = {Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans},
journal = {ACS Catalysis},
year = {2020},
volume = {10},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acscatal.0c02143},
number = {19},
pages = {11466--11480},
doi = {10.1021/acscatal.0c02143}
}
Cite this
MLA
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Karlinskii, Bogdan Ya., et al. “Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans.” ACS Catalysis, vol. 10, no. 19, Sep. 2020, pp. 11466-11480. https://doi.org/10.1021/acscatal.0c02143.