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%.