ChemInform Abstract: Controlled Synthesis of Functionalized Mixed Thiophene/Furan Oligomers

A novel and simple synthetic route for the preparation of a series of functionalized mixed thiophene/furan oligomers is described. This method, involving a Mn(OAc)3-mediated oxidative addition of β-thienyl-β-keto esters (=β-oxothiophenepropanoates) to methyl 3-thienylprop-2-enoates, allows the construction of highly functionalized heteropolyaromatic oligomers possessing various chain lengths (Schemes 2, 4, and 5). Moreover, the straightforward transformation of the carbonyl functions appended to the furan rings leads to polycarboxylic acid precursors of H2O-soluble conducting polymers (Scheme 6).