Solvent effect in palladium-catalyzed allylation of norbornadiene

The palladium-catalyzed allylation of norbornadiene is a unique method for the C-C bond formation involving allyl derivatives. This reaction proceeds in solution. However, the selection of the solvent is so far an empirical procedure, and the role of the solvent in this process is poorly understood....

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Bibliographic Details
Published in:Russian chemical bulletin 2021, Vol.70 (1), p.113-121
Main Authors: Durakov, S. A., Melnikov, P. V., Martsinkevich, E. M., Smirnova, A. A., Shamsiev, R. S., Flid, V. R.
Format: Article
Language:English
Subjects:
Allyl compounds
Chemical reactions
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Empirical analysis
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Inorganic Chemistry
Organic Chemistry
Palladium
Reagents
Solvent effect
Solvents
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Summary:The palladium-catalyzed allylation of norbornadiene is a unique method for the C-C bond formation involving allyl derivatives. This reaction proceeds in solution. However, the selection of the solvent is so far an empirical procedure, and the role of the solvent in this process is poorly understood. The effect of the solvent on the reaction pattern is considered in terms of polarity, polarizability, and coordinating ability of the solvent. These properties were shown to be the key factors in selecting the proper solvent. Based on investigation of the mechanism of individual catalytic cycle stages, the features of the interaction between the solvent, the catalyst, and reagents were analyzed.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-021-3064-z