1: With n-butyllithium in diethyl ether; hexane T=-78°C; Metallation; 2: With boric acid trimethyl ester in diethyl ether; hexane T=-70 - 10°C; boronation; 3: With hydrogenchloride in diethyl ether; hexane Hydrolysis;

n-butyllithium in diethyl ether; hexane n-BuLi (2.5 M, hexane) was added to C6F2BrH3 iN Et2O at -60 °C,stirring (-60--70 °C, 1 h), 1.5 equiv. of B(OMe)3 was added in E t2O (-70 °C, 30 min), stirring at -60--70 and 20 °C for 1 h and 30-40 min, resp.; poured into 5 percent HCl, org. layer was sepd., aq. layer was extd. with ether, extracts were combined, dried with MgSO4, evapn., recrystn. from hot toluene, elem. anal.;

1: nBuLi / tetrahydrofuran / -78 - 20 °C 2: H+ / 20 °C View Scheme

1: water; sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / ethylene glycol dimethyl ether / 48 h / 110 °C 2: hydrogenchloride; water / 1,4-dioxane / 72 h / 100 °C View Scheme

in methanol; water 33percent H2O in MeOH, 20 °C, several h; monitored by (19)F NMR;

tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide in tetrahydrofuran; water T=24°C; Suzuki-Miyaura Coupling; 0.0833333 h; Flow reactor;

1: 82 percent / K[HF2] / methanol; H2O / 1 h / 20 °C 2: BF3 / CH2Cl2 / -50 - -40 °C View Scheme

dihydrogen peroxide in diethyl ether T=20°C;

1: H2O2 / diethyl ether / 20 °C 2: 71.7 percent / Br / acetic acid / 4 h / 0 - 20 °C View Scheme

potassium phosphate; 2nd generation X-Phos precatalyst in tetrahydrofuran; water T=20°C; Suzuki-Miyaura cross-coupling; 0.5 h; Inert atmosphere;