[reaction: see text] The regioselective palladium(0)-catalyzed arylation of 3-furoate and 3-thiophenecarboxylate esters with aryl bromides is described. Conditions were developed that allow for the selective synthesis of either 2-aryl or 5-aryl products.

The triple reuptake inhibitor, GSK1360707, was synthesized via an efficient, scalable route, which features a vinyl triflate Suzuki coupling followed by a single-step, double alkylative cyclopropanation with a dihalomethane. Also, a mechanistic understanding of the Suzuki reaction (as it relates to the control of a polychlorinated biphenyl impurity) is discussed.

Furan derivatives Furan derivatives R 0060Regioselective Palladium-Catalyzed Arylation of 3-Carboalkoxy Furan and Thiophene. -Using Pd(PPh3)4 as the catalyst, formation of 2-aryl-substituted isomers is favored. If the reaction is accomplished using palladium on activated carbon, a mixture of 2-aryl and 5-aryl isomers is obtained. Treatment of (I) with bromobenzene gives no reaction while reaction of thiophene results in formation of the desired 2-phenylthiophene product (IX). The new method can also be applied for an efficient two-step synthesis of furoquinolinone (XII). -(GLOVER, B.; HARVEY, K. A.; LIU, B.; SHARP*, M. J.; TYMOSCHENKO, M. F.; Org. Lett. 5 (2003) 3, 301-304; Chem. Dev., GlaxoSmithKline, Research Triangle Park, NC 27709, USA; Eng.) -S. Adam 24-088