Organometallics
Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation
Egor L. Dolengovski
1
,
Tatyana V Gryaznova
1
,
Yulia B. Dudkina
1
,
Daut R. Islamov
2
,
R. А. Fayzullin
1
,
Oleg G. Sinyashin
1
,
Publication type: Journal Article
Publication date: 2023-04-20
Journal:
Organometallics
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The mechanistic details of the oxidative coupling of compounds with a number of different redox centers are investigated using N-(quinolin-8-yl)-benzamide (L) as a model substrate. The control of the chemical or electrooxidation parameters in the absence or presence of a cobalt catalyst makes it possible to obtain regioselectively different oxidative coupling products (ortho- vs para-C–H/C–H vs C–H/N–H vs N–H/N–H). The results indicate that the operative mechanism depends on the type of oxidized reaction center and the oxidant nature. Oxidation affects the para-C–H bond in quinoline or the N–H fragment or the ortho-C–H bond in the benzene substituent in the molecule. The intermediate Co(II)[L–H]2 complex and C–H-activated CoIII metallacycle with benzamide ligands, which are shown to oxidize at close potentials, have been isolated and characterized by various techniques, including X-ray diffraction and voltammetry. The strength of the oxidizing agent affects the formation of a particular product, though not acting as the determining factor. Two-electron oxidation of Co(II)[L–H]2 yields to C–N coupling, but one-electron oxidation of Co(III) leads to ortho-C–C coupling. All electrochemical reactions are performed under mild conditions at room temperature without adding special reagents (oxidants, halides, phosphines, etc.).
Top-30
Citations by journals
1
|
|
Green Chemistry
1 publication, 50%
|
|
Russian Chemical Reviews
1 publication, 50%
|
|
1
|
Citations by publishers
1
|
|
Royal Society of Chemistry (RSC)
1 publication, 50%
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 50%
|
|
1
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2023],"ids":[0],"codes":[0],"imageUrls":[""],"datasets":[{"label":"Citations number","data":[2],"backgroundColor":["#3B82F6"],"percentage":["100"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Green Chemistry","Russian Chemical Reviews"],"ids":[1017,23802],"codes":[0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[1,1],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":[50,50],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Royal Society of Chemistry (RSC)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[123,9422],"codes":[0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[1,1],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":[50,50],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2023],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0],"percentage":["0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0],"percentage":["0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0],"percentage":["0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2],"percentage":["100"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0],"percentage":["0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2023],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0],"percentage":["0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0],"percentage":["0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0],"percentage":["0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2],"percentage":["100"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0],"percentage":["0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
Dolengovski E. L. et al. Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation // Organometallics. 2023.
GOST all authors (up to 50)
Copy
Dolengovski E. L., Gryaznova T. V., Dudkina Y. B., R. Islamov D., Fayzullin R. А., Sinyashin O. G., Budnikova Y. H. Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation // Organometallics. 2023.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.organomet.2c00654
UR - https://doi.org/10.1021/acs.organomet.2c00654
TI - Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation
T2 - Organometallics
AU - Dolengovski, Egor L.
AU - Gryaznova, Tatyana V
AU - Dudkina, Yulia B.
AU - R. Islamov, Daut
AU - Fayzullin, R. А.
AU - Sinyashin, Oleg G.
AU - Budnikova, Yulia H.
PY - 2023
DA - 2023/04/20 00:00:00
PB - American Chemical Society (ACS)
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex
Copy
@article{2023_Dolengovski,
author = {Egor L. Dolengovski and Tatyana V Gryaznova and Yulia B. Dudkina and Daut R. Islamov and R. А. Fayzullin and Oleg G. Sinyashin and Yulia H. Budnikova},
title = {Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation},
journal = {Organometallics},
year = {2023},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.organomet.2c00654},
doi = {10.1021/acs.organomet.2c00654}
}