Effect of Alkoxy Substituents on the Regioselectivity of Catalytic C-H Activation in Benzoic Acids: Experimental and DFT Study

This work demonstrates the influence of the catalyst and alkyne nature on the regioselectivity of rhodium-catalyzed annulation of alkoxy-substituted benzoic acids (such as 3-methoxybenzoic, 3,4-dimethoxybenzoic, and piperonylic acids) with alkynes. Here, X-ray diffraction and DFT calculation data ga...

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Bibliographic Details
Published in:Catalysts 2023-02, Vol.13 (2), p.389
Main Authors: Kharitonov, Vladimir B., Muratov, Dmitry V., Nelyubina, Yulia V., Loginov, Dmitry A.
Format: Article
Language:English
Subjects:
Acids
Alkynes
Benzoic acid
C-H activation
Catalysis
Catalysts
Chemical bonds
Chemical reactions
Heterocyclic compounds
homogeneous catalysis
isocoumarins
Ligands
methoxy directing group
Regioselectivity
Rhodium
Substitutes
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Summary:This work demonstrates the influence of the catalyst and alkyne nature on the regioselectivity of rhodium-catalyzed annulation of alkoxy-substituted benzoic acids (such as 3-methoxybenzoic, 3,4-dimethoxybenzoic, and piperonylic acids) with alkynes. Here, X-ray diffraction and DFT calculation data gave evidence that the observed regioselectivity is provided by both steric and coordination effects of methoxy groups. The latter is the result of weak non-covalent C–H⋯O interactions with the supporting ligand rather than with the rhodium atom. We believe that these results are also valid for other reactions of the C-H activation of methoxy-substituted arene compounds.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal13020389