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Synlett 2020; 31(10): 1015-1021
DOI: 10.1055/s-0040-1708003
DOI: 10.1055/s-0040-1708003
letter
Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles
This work has been partially supported by the Institut National des Sciences Appliquées Rouen (INSA), the Rouen University, the Centre National de la Recherche Scientifique (CNRS), the EFRD, the European Interreg IV A France (Channel), and Labex SynOrg (ANR-11-LABX-0029).
Further Information
Publication History
Received: 05 February 2020
Accepted after revision: 29 February 2020
Publication Date:
17 March 2020 (online)
Abstract
The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1708003.
- Supporting Information
-
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For recent reviews, see:
For selected C–H arylation of imidazoles or their ring-fused analogues catalyzed by rhodium, copper, or nickel metals, see:
For reviews on this topic, see:
For palladium-catalyzed intramolecular direct arylation of imidazole, see:
For palladium-catalyzed intermolecular direct arylation of imidazole derivatives, see:
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