Palladium-Catalyzed Polycondensation for the Synthesis of Poly(Aryl)Sulfides.

The palladium-catalyzed CS cross coupling reaction is investigated as a novel efficient tool for the synthesis of poly(phenyl)sulfide derivatives. The reaction proceeds through the polycondensation of dibromo arenes with a H S-surrogate to yield poly(aryl)sulfides. The reaction is generalized by the synthesis of so-far-unprecedented poly(2,5-thiophene)sulfide.

Heteroacene Synthesis through C-S Cross-Coupling/5-endo-dig Cyclization.

Highly efficient, one-step synthesis of sulfur-containing heteroacenes was achieved through palladium-catalyzed C-S cross-coupling of bis-alkynes with thioacetate as hydrogen sulfide surrogate. Heteroacenes consisting of three, five, and seven fused aromatic rings were obtained in a single catalytic step by four-, six-, and eightfold C-S bond formation.

Ambidextrous catalytic access to dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by both palladium-catalyzed C-S and oxidative dehydro C-H coupling.

A modular two-step synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d']thieno[3,2-b;4,5-b']dithiophene (DBTDT) and associated two donor (anisyl) and acceptor (acetyl) substituted DTT derivatives were synthesized by palladium-catalyzed cross-coupling sequences in 17% to 71% yield over two steps. The 5,5'-disubstituted DTT derivatives were characterized in terms of their photophysical (UV and fluorescence spectroscopy) and electrophysical (cyclovoltammography) properties.