Pd0(tris(tert-butyl)phosphine)2; potassium hydroxide in 1,4-dioxane; water T=25°C; Suzuki-Miyaura coupling; 3 h; Inert atmosphere; chemoselective reaction;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in 1,4-dioxane T=80°C; Suzuki cross-coupling reaction; 18 h;

potassium acetate in toluene mixt. of B compd., aryl halide, Pd(dba)2 complex, (4-MeOC6H4)3P, KOAc and toluene stirred for 24 h at 80°C;

catalyst: [Ir(COD)Cl]2/8bpy in o-xylene under Ar; o-xylene (60 mmol) added to pinacolborane (2 mmol) + 1.5 molpercent (Ir(COD)Cl)2 + bpy; stirred (80°C, 6 h); solvent removed (vac., room temp.); residue chromd. (silica gel, CH2Cl2); elem. anal.;

magnesium; triethylamine in tetrahydrofuran Barbier-type reaction; 15 h; Inert atmosphereReflux;

palladium on activated charcoal T=100°C; 16 h;