UNEXPECTED EFFECT OF N-HETEROCYCLIC CARBENE ON THE CATALYTIC ACTIVITY OF PALLADIUM COMPLEX IN THE CROSS-COUPLING REACTION OF K[C 6 F 5 BF 3 ] WITH ARYL CHLORIDES

N. Yu. Adonin; Адонин Н. Ю.; A. Yu. Shabalin; Шабалин А. Ю.; S. A. Prikhod’ko; Приходько С. А.; V. V. Bardin; Бардин В. В.

doi:10.31857/S2686953522600829

UNEXPECTED EFFECT OF N-HETEROCYCLIC CARBENE ON THE CATALYTIC ACTIVITY OF PALLADIUM COMPLEX IN THE CROSS-COUPLING REACTION OF K[C₆F₅BF₃] WITH ARYL CHLORIDES

Authors: Adonin N.Y.¹, Shabalin A.Y.¹, Prikhod’ko S.A.¹, Bardin V.V.²
Affiliations:
1. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences
2. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Issue: Vol 513, No 1 (2023)
Pages: 29-33
Section: CHEMISTRY
URL: https://journals.eco-vector.com/2686-9535/article/view/651927
DOI: https://doi.org/10.31857/S2686953522600829
EDN: https://elibrary.ru/BCXHTV
ID: 651927

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Abstract

In the presence of the precursor of carbene SIMes, the yields of pentafluorobiphenyls in the palladium-catalyzed cross-coupling of potassium pentafluorophenyltrifluoroborate with aryl chlorides decrease while under the same conditions yield of 2,3,4,5,6-pentafluoro-4′-methylbiphenyl from 4-bromotoluene increases. An explanation for this phenomenon is proposed, as well as for the intensification of the side hydrodeboration reaction of the initial borate.

Keywords

cross-coupling, aryl bromides, aryl chlorides, N-heterocyclic carbenes, pentafluorophenyltrifluoroborate, palladium catalyst

About the authors

N. Yu. Adonin

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Author for correspondence.
Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

A. Yu. Shabalin

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

S. A. Prikhod’ko

Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

V. V. Bardin

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: adonin@catalysis.ru
Russian, 630090, Novosibirsk

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