Studies Towards The Synthesis of 2,5-Disubstituted-3-Flurothiophenes Using a Tandem Directed Ortho Metallation/Nickel Catalyzed Cross-Coupling Approach03/15/2016
2,5-Disubstituted 3-fluorothiophene derivatives are of interest as building blocks in liquid crystal materials synthesis. This poster details the development of 2-thienyl carbamates and related compounds as flexible building blocks for the construction of 2,5-disubstituted 3-fluorothiophenes. Our approach involves oxidation of 5-substituted 2-thienyl trifluoroborates to the corresponding thienones followed by O-trapping of the corresponding enolate as the 2-thienyl carbamate. Studies aimed at the elaboration of to 2,5-disubstituted 3-fluorothiophenes using a sequential directed ortho-metalation/fluorination/Ni-catalyzed cross-coupling approach will be presented.