Unexpected Effect of N-Heterocyclic Carbene on the Catalytic Activity of Palladium Complex in the Cross-Coupling Reaction of K[C6F5BF3] with Aryl Chlorides

In the palladium-catalyzed cross-coupling of potassium pentafluorophenyltrifluoroborate with aryl chlorides in the presence of the precursor of SIMes carbene, the yields of pentafluorobiphenyls decrease, whereas the yield of 2,3,4,5,6-pentafluoro-4'-methylbiphenyl from 4-bromotoluene under the...

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Bibliographic Details
Published in:Doklady. Chemistry 2023-11, Vol.513 (1), p.337-341
Main Authors: Adonin, N. Yu, Shabalin, A. Yu, Prikhod’ko, S. A., Bardin, V. V.
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbenes
Catalytic activity
Chemical reactions
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chlorides
Cross coupling
Industrial Chemistry/Chemical Engineering
Palladium
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Summary:In the palladium-catalyzed cross-coupling of potassium pentafluorophenyltrifluoroborate with aryl chlorides in the presence of the precursor of SIMes carbene, the yields of pentafluorobiphenyls decrease, whereas the yield of 2,3,4,5,6-pentafluoro-4'-methylbiphenyl from 4-bromotoluene under the same conditions increases. An explanation for this phenomenon and for the intensification of the side hydrodeboration reaction of the initial borate has been proposed.
ISSN:0012-5008
1608-3113
DOI:10.1134/S0012500823600979