Domino reactions are essential for advancing organic synthesis. This study introduces
novel thioamide-based precursors for a palladium-catalyzed selective domino heteroarylation
process. The method efficiently produces benzothieno[2,3-b]quinolones with yields ranging from moderate to very good. By employing aryl chlorides,
the efficiency of the domino hetero-annulation process is comparable to that of aryl
bromides. Executing a one-pot, two-step reaction also delivered a single domino product
with high selectivity. The strategy involved fine-tuning substituent reactivity, utilizing
electron-rich arenes, and forming metallocycles with nucleophilic sulfur, consistently
yielding a single product. The proposed mechanism is corroborated by mechanistic studies.
Key words
domino reaction - benzothiophene - palladium - selective C–S and C–N bond formation
