Synthesis of functionalized thiophene/phenyl co-oligomers by direct arylation of thiophenes

Abstract

π-Conjugated rod-like molecules have proven to be powerful candidates for the generation of well-defined nanostructures with interesting optical and optoelectrical properties. Their synthesis, however, turns out to be rather complex in some cases. Here, we have optimized the synthesis of oligomers consisting of thiophene and phenylene groups with three or four aromatic units using a direct arylation approach, which allows us to use cheap starting materials and to minimize the number of reaction steps considerably.

Sustainable protocols for direct C–H bond arylation of (hetero)arenes

“…In the same year, Lützen et al proposed the use of H 2 O/ THF mixture for the direct C-H bond arylations of α-substituted thiophenes 153 with functionalized iodobiphenyls 154: the reactions were performed with Pd(dppf )Cl 2 , PPh 3 and Ag 2 CO 3 , affording the thiophene/phenylene systems 155 in 53-84% yields (Scheme 60). 189 Despite the use of an aqueous reaction medium, in our opinion this protocol does Scheme 57 C2 regioselective direct C-H bond arylation of furan 146 with aryl diazonium salts performed in water as the solvent.…”