Fig. 3: Monoarylation and diarylation of anthracene with various fluoroarenes.
From: Birch reductive arylation by mechanochemical anionic activation of polycyclic aromatic compounds

a Isolated yield. b Reactions are conducted in a 50-mL stainless-steel jar using two 10-mm stainless-steel balls. The reaction time and temperature of ball-milling-II are 180 min and heated 70 °C (heat-gun preset temperature). c The reaction time of ball-milling-II is 6 h. d The reaction time of ball-milling-II is 8 h. e The reaction time of ball-milling-II is 120 min. f 1.6 equivalent of 9-fluoroanthracene is used.