Fluorobenzene

Raney Ni (RTH-3110) and 5% Pd/C catalyst used in this study were purchased from Dalian Tongyong Chemical Co., Ltd., Liaoning, China. The weight percentage of nickel and aluminum in the catalyst were more than 90% and less than 7%, respectively. Raney Ni and Pd/C catalyst are not pre-treated before all experiments, and they were kept in water-sealing storage and hermetical desicator, respectively.
All HACs including fluorobenzene (FB), chlorobenzene (CB), bromobenzene (BB), iodobenzene (IB), 4-fluorophenol (4-FP), 4-chlorophenol (4-CP), 4-bromophenol (4-BP), and 4-iodophenol (4-IP) used in experiments were purchased from Sigma-Aldrich with a minimum purity of 98%. The other reagents such as EtOH, NaOH, NaF, NaCl, NaBr, and NaI are analytical grade and supplied by Sinopharm Chemical Reagent Co., Ltd., Shanghai, China. Deionized water was used in the reaction. The purity of hydrogen and nitrogen used in the experiments is more than 99.99%.

Dopamine hydrochloride (99%, DA), 2,3-dichloromaleic anhydride (97%), 1-hexylamine (99%), sodium citrate tribasic (≥99%), and fluorobenzene were purchased from Sigma-Aldrich (Sydney, Australia) and used as received without any further purification. Silver nitrate and triethylamine (TEA) were purchased from Univar (Sydney, Australia) and also used as received. 2,2′-azobis(isobutyronitrile) (AIBN, Sigma-Aldrich, 97%) was purified by recrystallization from cold methanol prior to use. Pentafluorostyrene (PFS, Oakwood Products, 99%) was passed through a column of activated basic alumina prior to use to remove inhibitor. 4-cyanopentanoic acid dithiobenzoate (CPADB) was synthesized as described in the literature [22 (link)]. 1-thio-β-ᴅ-glucose sodium salt (GluSNa) was prepared from 1-thio-β-ᴅ-glucose tetraacetate (AcO-GluSH) according to literature method [23 (link)]. All solvents were laboratory reagent grade and used as received without any further purification.