Thienyl-thienyl coupling with regioselectivity control is arguably one of the most important transformation for organic p-electronic materials science as evidenced by a diversity of small molecular, oligomeric, and polymeric semi-conductive materials containing thiophene-thiophene linkage. This transformation is ideally achieved through direct C–H/C–H coupling. However, direct transition-metal-catalyzed regioselective oxidative C–H/C–H coupling conditions are hardly compatible for various p-units of importance in optoelectronic materials sciences especially for donor materials because these p-units are not redox innocent that interferes an oxidative catalytic cycle, and the catalyst efficacy are hardly sufficient enough to enable direct C–H/C–H polymerization of them to achieve the “holy grail” in synthesis of optoelectronic polymer. We found that an iron(III) salt in combination with tridentate phosphine ligand and trimethylaluminum as base selectively cleaves thienyl C–H bond at C2 position and allows regioselective thienyl-thienyl coupling of high efficiency using a very mild oxalate as oxidant for catalyst turnover. The reaction is compatible with various p-units generally found in optoelectronic materials and is accelerated by ligand optimization to allow C–H/C–H polycondensation to allow synthesis of various small molecular, oligomeric and polymeric semiconductive materials of importance in energy device applications.

Iron-catalyzed Regioselective Thienyl C-H/C-H Coupling and Polycondensation for Organic Electronic Materials

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