Sonogashira coupling with aryl chlorides under the high-temperature ball-milling conditions^a.

^aConditions: 1 (0.45 mmol), 2 (0.30 mmol), Pd(OAc)₂ (0.015 mmol), BrettPhos (0.0225 mmol), DABCO (0.45 mmol), H₂O (0.4 μL mg⁻¹) in a stainless-steel ball-milling jar (1.5 mL).

^b10 mol% of Pd(OAc)₂, 15 mol% of BrettPhos, and 3.0 equiv. of DABCO were used.