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Synthesis 2023; 55(21): 3526-3534
DOI: 10.1055/s-0041-1738433
DOI: 10.1055/s-0041-1738433
special topic
C–H Bond Functionalization of Heterocycles
Palladium-Catalyzed C7–H (Hetero)arylation of Pyrazolo[1,5-a]pyrazines with Heteroarenes and Aryl Iodides with the Assistance of Silver Salts
L.P. and A.L. are grateful to Erasmus and Grand Est (Alsace region) for financial support during their internship stay at AstraZeneca (AZ).

Abstract
Pyrazolo[1,5-a]pyrazines coupled with heteroarenes and aryl iodides selectively at the C7 position to afford a broad library of bi(hetero)aryl structures under ligand-free palladium-catalyzed conditions. The key to the success of the reaction is the use of silver salts as the oxidant or the base, allowing the regioselective C–H bond functionalization to occur under relatively mild conditions.
Key words
C–H bond functionalization - fused-ring systems - heteroarenes - homogeneous catalysis - synthetic methodsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738433.
- Supporting Information
Publikationsverlauf
Eingereicht: 13. Dezember 2022
Angenommen nach Revision: 30. Januar 2023
Artikel online veröffentlicht:
06. März 2023
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Several reviews on C–H arylation, see:
Formation of (hetero)arene-Ag complex was generally proposed when silver salt was indispensable for C–H bond cleavage (experimentally confirmed when Ag salt was crucial for H/D exchange), for example, see:
Silver cation could act as iodide scavenger to remove iodide from palladium, see: