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Direct C–H Bond Arylation of Thienyl Thioamides Catalyzed by Pd–Phenanthroline Complexes

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posted on 06.11.2015, 00:00 by Takayuki Yamauchi, Fumitoshi Shibahara, Toshiaki Murai
A direct C–H bond arylation method for thienyl thioamides catalyzed by [Pd­(phen)2]­(PF6)2 was developed. This reaction selectively afforded 2-monoarylated products, while the corresponding amide thiophene derivatives furnished 2,5-diarylated products. Mechanistic studies revealed that a Pd­(II)–bisthioamide complex should be the active species for the reaction of thienyl thioamides in the presence of catalytic amounts of [Pd­(phen)2]­(PF6)2. Similar to the reaction with amides, the reaction with thioamides selectively generated the 2,5-diarylated products when a preformed Pd­(phen)­PhI complex was used.