Tetrakis triphenylphosphine palladium

All reagents were used as received, without further purification. Hydrogen tetrachloroaurate(III) tetrahydrate (HAuCl₄·4H₂O, 99.0%) was purchased from Kanto Chemical Co., Inc. Silver(I) nitrate (AgNO₃, >99.9%) was purchased from Kojima Chemicals Co., Ltd. Tetrabutyl ammonium bromide {TBABr, [N(C₄H₉)₄]Br, >98.0%}, triethylamine [N(C₂H₅)₃, >99.0%], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄, >97.0%], and tetrakis(triphenylphosphine)platinum(0) [Pt(PPh₃)₄, >97.0%] were purchased from Tokyo Chemical Industry Co., Ltd. Sodium borohydride (NaBH₄, 95.0%), triphenylphosphine (PPh₃, 97.0%), 12 molybdo(VI) phosphoric acid n-hydrate [H₃(PMo₁₂O₄₀)·nH₂O, >95.0%], disodium molybdate(VI) dihydrate (Na₂MoO₄·2H₂O, >99.0%), disodium tungstate(VI) dihydrate (Na₂WO₄·2H₂O, 99.0%–100.5%), hydrochloric acid (HCl, 35.0%–37.0%), and acetic anhydride [(CH₃CO)₂O, >97.0%] were purchased from Wako Pure Chemical Industry.

1,2-Dichlorocyclopentane, n-butyl lithium solution, and tris(dibenzylideneacetone) dipalladium(0)-chloroform adduct were purchased from Sigma-Aldrich Co., Ltd. Cesium fluoride and tetrakis(triphenylphosphine)palladium were purchased from Tokyo Chemical Industry. 3-Bromo-2-methylthiophene, acetonitrile, and 4-pyridylboronic acid were purchased from Wako Pure Chemical Industries, Ltd. Triisopropyl borate, N-bromosuccinimide, acetic acid, ethyl acetate, hexane, methanol (MeOH), Na₂CO₃, NaOH and MgSO₄ were purchased from Nacalai Tesque. Tetrahydrofuran (THF) and DMF were purified by utilizing a Glass Contour solvent dispending system. Other reagents were reagent grade and used without further purification. 2-Methyl-3-thienylboronic acid and non-substituted DTE (compound 1) was synthesized according to the procedures of Shinokubo et al.^{49 (link)} 1,2-Bis(2′-methyl-5′-bromothien-3′-yl)perfluorocyclopentene (compound 2) was prepared from compound 1 by reacting with N-bromosuccinimide according to the method reported by Park et al.^{50 (link)}