Article Dans Une Revue (Article De Synthèse) Advanced Synthesis and Catalysis Année : 2024

Regioselective C6‐Arylation of Thieno[3,2‐ c ]pyrazole Heterocycles with Aryl Iodides

Résumé

Abstract Regioselective C6‐arylation of thieno[3,2‐ c ]pyrazoles with aryl iodides as coupling partners has been developed. This strategy was performed in the presence of Pd(OAc) 2 as catalyst in combination with AgOTf as an oxidant and TFA in dimethylacetamide. In all experiments, only the C6‐arylated thieno[3,2‐ c ]pyrazole was isolated since its C5‐regioisomer was not observed, indicating the high regioselectivity of this approach. The catalytic system used is compatible with a variety of 3‐functionalized thieno[3,2‐ c ]pyrazoles and iodoaryl electrophiles, providing access to 3,6‐disubstituted thieno[3,2‐ c ]pyrazoles in yields ranging from 49% to 94%.

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Dates et versions

hal-04833816 , version 1 (12-12-2024)

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Noura Ait Lfakir, Badr Jismy, Gérald Guillaumet, Mohamed Akssira, Ahmed El Hakmaoui, et al.. Regioselective C6‐Arylation of Thieno[3,2‐ c ]pyrazole Heterocycles with Aryl Iodides. Advanced Synthesis and Catalysis, 2024, 366 (12), pp.2749-2757. ⟨10.1002/adsc.202400141⟩. ⟨hal-04833816⟩
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