1-Chloro-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2,-dioxaborolan-2-yl)benzene and 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indole could be produced through the following synthetic routes.

A. 1-Chloro-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2,-dioxaborolan-2-yl)benzene. A 50-mL, two-necked, round-bottomed flask is fitted with a magnetic stirring bar, a rubber septum, and a condenser to which a nitrogen inlet and an oil bubbler are attached, and flushed with nitrogen . The septum is removed and the flask is charged with bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(l) ([Ir(OMe)(COD)]₂) (33 mg, 0.050 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (dtbpy) (27 mg, 0.10 mmol), and bis(pinacolato)diboron (2.67 g, 10.5 mmol). The septum is again placed on the flask, and the flask is purged with nitrogen for 1 min. Hexane (30 mL) is added by syringe, and the flask is immersed in an oil bath that is maintained at 50 °C. The mixture is stirred for 10 min to give a dark red solution. The flask is charged with 1-chloro-3-iodobenzene (4.75 g, 19.9 mmol) by syringe, and then the resulting dark red solution is stirred at 50 °C for 6 hr. The mixture is removed from the oil bath, allowed to cool to room temperature, and poured into a separatory funnel. The reaction flask is rinsed with hexane (2 × 10 mL). The rinses and water (30 mL) are added to the separatory funnel, the funnel is shaken, the layers are separated, and the organic extracts are dried over anhydrous magnesium sulfate. The drying agent is removed by filtration and is washed with hexane (3 × 10 mL), and the filtrate is concentrated on a rotary evaporator to give a dark brown oil. The oil is distilled under reduced pressure to afford 6.11-6.20 g (84-86%) of 1-chloro-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene as a white solid, mp 58.6-60.7 °C.

B. 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indole. A 50-mL, two-necked, round-bottomed flask is fitted with a magnetic stirring bar, a rubber septum, and a condenser to which a nitrogen inlet and an oil bubbler are attached, and flushed with nitrogen The septum is removed and the flask is charged with bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(l) ([Ir(OMe)(COD)]₂) (50 mg, 0.075 mmol) and 4,4'-di-tert-butyl-2,2'-bipyridine (dtbpy) (40 mg, 0.15 mmol). The septum is again placed on the flask, and the flask is purged with nitrogen for 1 min. Hexane (30 mL) and pinacolborane (4.79 mL, 33.0 mmol) are added by syringe, and the flask is immersed in an oil bath that is maintained at 25 °C. The mixture is stirred for 10 min. to give a dark red solution. The flask is charged with indole (3.51 g, 30.0 mmol), and then the resulting dark red suspension is stirred at 25 °C for 4 hr. The mixture is removed from the oil bath, allowed to cool to room temperature, and poured into a separatory funnel. The reaction flask is rinsed with ether (2 × 20 mL). The rinses and water (30 mL) are added to the separatory funnel, the funnel is shaken, the layers are separated, and the organic extracts are dried over anhydrous magnesium sulfate. The drying agent is removed by filtration and is washed with ether (3 × 10 mL), and the filtrate is concentrated on a rotary evaporator to give a dark brown oil. The oil is distilled under reduced pressure to afford 5.33-5.40 g (73-74%) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole as a colorless viscous oil, bp 149-153 °C (0.15 mm).

Notice: The reactions produce hydrogen gas and should be conducted in a well-ventilated hood.