Distinguishing between Homogeneous and Heterogeneous Catalytic Activity in C–H Arylation of an Indole with Aryl Halides under “Ligandless” Conditions: Crucial Evidence from Real Catalytic Experiments

The kinetic approach for distinguishing between homogeneous and heterogeneous catalysis mechanisms by the analysis of differential selectivity was applied for direct C–H arylation of an indole with aryl halides under “ligandless” conditions. The differential selectivity of competing arylation of an...

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Bibliographic Details
Published in:Organic process research & development 2019-05, Vol.23 (5), p.1052-1059
Main Authors: Yarosh, Elena V, Kurokhtina, Anna A, Larina, Elizaveta V, Lagoda, Nadezhda A, Schmidt, Alexander F
Format: Article
Language:English
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Summary:The kinetic approach for distinguishing between homogeneous and heterogeneous catalysis mechanisms by the analysis of differential selectivity was applied for direct C–H arylation of an indole with aryl halides under “ligandless” conditions. The differential selectivity of competing arylation of an indole with two aryl iodides or bromides and the differential regioselectivity of a parallel formation of C2- and C3-regioisomers of arylated indoles were studied by the simple method of phase trajectories needed for raw kinetic data only. The results obtained indicated that the selectivities strongly depended on the type (soluble or insoluble) and concentration of the Pd precursor. Considering the pathways of Pd transformations under the reaction conditions, this indicates a substantial contribution of catalysis occurring on the surface of metallic Pd (including nanoparticles).
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00096