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
| Autor: | A. A. Kurokhtina, Alexander F. Schmidt, N. A. Lagoda, E. V. Larina, E. V. Yarosh |
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| Rok vydání: | 2019 |
| Předmět: |
Indole test
010405 organic chemistry Aryl Organic Chemistry Halide chemistry.chemical_element Regioselectivity 010402 general chemistry Heterogeneous catalysis 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Selectivity Palladium |
| Zdroj: | Organic Process Research & Development. 23:1052-1059 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/acs.oprd.9b00096 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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