jo201770j_si_001.pdf (2.3 MB)
Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles via Pd-Mediated Decarboxylative Cross-Coupling
journal contribution
posted on 2011-11-04, 00:00 authored by Frank
A. Arroyave, John R. ReynoldsA general scheme for the synthesis of π-conjugated
molecules
based on 3,4-dioxypyrroles is presented. The π-conjugated molecules
were synthesized via Pd-mediated decarboxylative
cross-coupling using various 3,4-propylenedioxypyrrole carboxylic
acids and aryl bromides, including the base-sensitive electron acceptor
4,7-dibromobenzo[c][1,2,5]thiadiazole (BTD). N-Methylpyrrolidone was used as solvent, Pd(acac)2 was employed as the palladium source and P(o-tol)3 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%.