1: With sodium carbonate in water; N,N-dimethyl-formamide 0.0833333 h; 2: With palladium diacetate in water; N,N-dimethyl-formamide T=20°C;

1: 4-fluoroaniline With tetrafluoroboric acid; sodium nitrite in water T=0 - 5°C; Diazotization; 0.5 h; 2: potassium (2-formylphenyl)trifluoroborate With bis(tri-o-tolylphosphine)palladium acetate in methanol T=20°C; Arylation; 4 h;

bis(tri-o-tolylphosphine)palladium acetate in methanol T=20°C; 4 h;

1.1: 91 percent / KHF2 / methanol; H2O / 20 °C 2.1: HBF4; NaNO2 / H2O / 0.5 h / 0 - 5 °C 2.2: 67 percent / Pd2(μ-OAc)2(P(o-tolyl)3)2 / methanol / 4 h / 20 °C View Scheme

dipotassium peroxodisulfate; tetraethylammonium bromide in 1,2-dichloro-ethane T=120°C; 36 h; Inert atmosphere;