1: 1,2-dibromo-4-iodobenzene With isopropylmagnesium chloride in tetrahydrofuran T=-78°C; 3 h; Inert atmosphere; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran T=-78 - 25°C; Inert atmosphere;

[Ir(C8H12)(OCH3)]2; 4,4'-di-tertbutylpyridine in further solvent(s) (N2); heating mixt. of iridium compd., bipyridine deriv., benzene deriv., dodecane and silylborane deriv. at 80°C for 4 h; cooling to room temp., chromy. (silica gel, diethyl ether in hexane (gradient from 0percent to 5percent)), NMR;

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

1.1: tetrafluoroboric acid; sodium nitrite / water / 0.5 h / 0 °C 2.1: potassium iodide / water; acetone / 0.5 h / 25 °C 3.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere 3.2: -78 - 25 °C / Inert atmosphere View Scheme

1.1: tetra-n-butylammonium tribromide / dichloromethane / 0.5 h / 25 °C 2.1: tetrafluoroboric acid; sodium nitrite / water / 0.5 h / 0 °C 3.1: potassium iodide / water; acetone / 0.5 h / 25 °C 4.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere 4.2: -78 - 25 °C / Inert atmosphere View Scheme

potassium fluoride in N,N-dimethyl-formamide T=50°C; 18 h; Inert atmosphere;