Microwave‐Assisted CH Activation of the Thiophene Ring: A Simple Approach to Access Substituted Thienopyridines

Campos, Joana F.; Cimorelli, Mélanie; Jemili, Rihab; Berteina‐Raboin, Sabine

doi:10.1002/slct.202101643

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2024

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“…[20] In 2018, Berteina et al . developed a direct C−H activation on thieno‐pyridines, ‐pyrimidines and ‐pyrazines with aryl halides exclusively at the α‐position of the thiophene ring (Scheme 1a) [20a,b] . However, in order to regioselectively achieve arylation at the C5‐position of thieno[2,3‐ d ]pyrimidines to the detriment of C6, Itami et al .…”

Section: Introductionmentioning

confidence: 99%

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

Ait Lfakir,

Jismy,

Guillaumet

et al. 2024

Adv Synth Catal

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Efficient and 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 novel 3,6‐disubstituted thieno[3,2‐c]pyrazoles in moderate to good yields.

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Section: Introductionmentioning

confidence: 99%