Preparation of the heterogeneous catalyst nickel-on-charcoal

The flask was attached to an argon purged distillation setup and placed in a preheated 175-180 °C sand bath above a stir plate. Once the distillation ended, the flask temperature rises automatically but should be held below 220 °C for an additional 15 minutes. 

Upon cooling to room temperature, the black solid was washed with water (2 x 50 mL) under argon into a pre-dried in vacuo 150-mL course fritted funnel. The 100 mL of water used to wash the Ni/C was removed via rotary evaporation 

METAL CATALYSED CARBON-CARBON BOND-FORMING REACTIONS 

In a 10-mL round-bottomed flask under argon triphenylphosphine (75 mg, 0.28 mmol, 0.4equiv.) and 0.75 mmol/g Ni/C (96 mg, 0.07 mmol, O.lequiv.) 

In a second flask K3PO4 (547 mg, 2.58 mmol, 3.6 equiv.), lithium bromide (150 mg, 1.73 mmol), phenylboronic acid (135 mg, 1.08 mmol, 1.5 equiv.) and 2-chlorobenzonitrile (99 mg, 0.72 mmol) were combined. 

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