Organometallics

Mechanism-Driven Development of N-(Quinolin-8-yl)-benzamide Coupling Reactions via C–H or N–H Activation

Dolengovski Egor L. ¹

Gryaznova Tatyana V ¹

Dudkina Yulia B. ¹

R. Islamov Daut ²

Fayzullin R. А. ¹

Sinyashin Oleg G. ¹

Budnikova Yulia H. ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan Scientific Center of the Russian Academy of Sciences

Kazan National Research Technological University, 68 Karl Marx Street, 420015 Kazan, Russia |

Publication type: Journal Article

Publication date: 2023-04-20

American Chemical Society (ACS)

Journal: Organometallics

Quartile SCImago

Quartile WOS

Impact factor: 2.8

ISSN: 02767333, 15206041

DOI: 10.1021/acs.organomet.2c00654

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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.).

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Green Chemistry	Green Chemistry, 1, 50% Green Chemistry 1 publication, 50%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 50% Russian Chemical Reviews 1 publication, 50%
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Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 50% Royal Society of Chemistry (RSC) 1 publication, 50%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 50% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 50%
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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.

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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.

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RIS Copy

TY - JOUR

DO - 10.1021/acs.organomet.2c00654

UR - https://doi.org/10.1021%2Facs.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 -

BibTex

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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%2Facs.organomet.2c00654},

doi = {10.1021/acs.organomet.2c00654}

}

Found error?

Publisher

American Chemical Society (ACS)

Journal

Organometallics

Quartile SCImago

Quartile WOS

Impact factor

2.8

ISSN

02767333 (Print)
15206041 (Electronic)

Labs

Laboratory of Electrochemical Synthesis

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