10.1021/jo201770j.s001 Frank A. Arroyave Frank A. Arroyave John R. Reynolds John R. Reynolds Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles <i>via</i> Pd-Mediated Decarboxylative Cross-Coupling American Chemical Society 2011 palladium source synthesis molecule pyridinyl units aryl bromides BTD dioxypyrrole 2011-11-04 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Conjugated_Molecules_Based_on_3_4_Dioxypyrroles_i_via_i_Pd_Mediated_Decarboxylative_Cross_Coupling/2589679 A general scheme for the synthesis of π-conjugated molecules based on 3,4-dioxypyrroles is presented. The π-conjugated molecules were synthesized<i> via</i> Pd-mediated decarboxylative cross-coupling using various 3,4-propylenedioxypyrrole carboxylic acids and aryl bromides, including the base-sensitive electron acceptor 4,7-dibromobenzo­[<i>c</i>]­[1,2,5]­thiadiazole (BTD). <i>N</i>-Methylpyrrolidone was used as solvent, Pd­(acac)<sub>2</sub> was employed as the palladium source and P­(<i>o</i>-tol)<sub>3</sub> as the ligand. The methodology was applied to 3,4-dioxypyrrole monoacids and 3,4-dioxypyrrole diacids to produce multi-ring π-conjugated systems containing phenyl, thiophenyl, BTD, and pyridinyl units. In general, the method has yielded a practical approach for the synthesis of 3,4-dioxypyrrole-based π-conjugated molecules in acceptable to high yields of 44–94%.