Synthesis 2023; 55(21): 3526-3534
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

a   Medicinal Chemistry, Research and Early Development, Respiratory and Immunology, BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden
,
Armand Levoin
a   Medicinal Chemistry, Research and Early Development, Respiratory and Immunology, BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden
b   University of Strasbourg, 4 Rue Blaise Pascal, 67081 Strasbourg, France
,
Lorenzo Poli
a   Medicinal Chemistry, Research and Early Development, Respiratory and Immunology, BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden
b   University of Strasbourg, 4 Rue Blaise Pascal, 67081 Strasbourg, France
› Institutsangaben
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.

Supporting Information



Publikationsverlauf

Eingereicht: 13. Dezember 2022

Angenommen nach Revision: 30. Januar 2023

Artikel online veröffentlicht:
06. März 2023

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