S‑Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2‑Arylpyridines and Heteroarenes

Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67–89% yields. This reagent is a...

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Veröffentlicht in:Journal of organic chemistry 2019-10, Vol.84 (20), p.13045-13052
Hauptverfasser: Sharma, Poonam, Jain, Nidhi
Format: Artikel
Sprache:eng
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Zusammenfassung:Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67–89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented insertion of an arylthio unit from both parts of the reagent (SPh and p-TolSO2) in the presence of copper acetate. Indoles and imidazopyridines also undergo facile reaction at the C-3 position and furnish thioarylated derivatives in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01954