Fig. 4: Substrate scope in arylation of PAHs and oxidation of dihydroanthracene to anthracene derivatives.
From: Birch reductive arylation by mechanochemical anionic activation of polycyclic aromatic compounds
a Indicated yields are isolated ones. b Step-B is conducted with o-chloranil (2.0 eq.) in benzene (10 mL). c step-B is conducted with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (4 eq.) after the ball-milling-II. d The reaction is conducted in a 5.0-mL stainless-steel jar using two 7-mm stainless-steel balls at a 1.0-mmol scale. e The reaction time of ball-milling-II is 6 h. f The reactions are conducted on a 0.12 mmol scale. g The reactions are conducted on a 0.15 mmol scale, and 2-fluoropyridine is used rather than fluorobenzene. Anthracene (1a), fluoranthene (6a), pyrene (6b), benzo[a]pyrene (6c), benzo[f]tetraphene(6e), tetracene(6f), and pentacene (6g) were used as starting materials.
