1: 3,5-diiodopyridine With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-78°C; 2 h; 2: MeOB(pin) in tetrahydrofuran T=-78 - 20°C;

ammonium chloride in tetrahydrofuran iPrMgCl*LiCl in THF added to soln. at -78°C of C5H3NI2 in THF in dry, argon-flushed Schlenk tube; mixt. stirred for 2 h, until I/Mg exchange; BO2(C(CH3)2)2(OCH3) added; allowed to warm to room. temp., 1 h; quenched with aq. soln. of NH4Cl; extrn. with Et2O; dried over Na2SO4; filtration, soln. evapd. in vac.;

1.1: 68 percent / 2 h / 68 °C 2.1: iPrMgCl*LiCl / tetrahydrofuran / 2 h / -78 °C 2.2: 76 percent / tetrahydrofuran / -78 - 20 °C View Scheme

1: 3,5-diiodopyridine With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-78°C; 2.5 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran T=-78 - 20°C;

[Ir2(OMe)2(1,5-cyclooctadiene)2]; dtbpy in tetrahydrofuran T=80°C; 18 h; Inert atmosphere; regioselective reaction;

1.1: copper(l) iodide; sodium iodide; N-methyl-2-(methylamino)ethylamine / 1,4-dioxane / 20 h / 120 °C / |Schlenk technique 2.1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 2.5 h / -78 °C 2.2: -78 - 20 °C View Scheme