(untitled) - Komeyama, K; Ohata, R; Kiguchi, S; Osaka, I (Chem. Commun., 2017)
4-Dodecylanisole (3aa) – Typical Procedure for One-Pot Arylation A 10 mL Schlenk tube was charged with dodecyl methyl sulfide (4a, 0.11 g, 0.50 mmol) and DCE (1.0 mL) before an addition of MeOTf (74 μL, 0.65 mmol). The resulting mixture was stirred for 12 h at 60 °C. After removal of all volatiles under reduced pressure (ca. 1 Torr), NiCl2(bpy) (7.1 mg, 0.025 mmol), CySH (6 μL, 0.050 mmol), and DMA (3.0 mL) were subsequently added to the tube. The resulting mixture was cooled to 0 °C, and a solution of 4-methoxyphenylzinc (2a, 0.56 M in THF, 1.8 mL, 1.0 mmol) was then added dropwise. The resulting mixture was stirred for 12 h at 0 °C before an addition of aqueous HCl (2 M). The resulting biphasic solution was extracted with a mixture of hexane and EtOAc (v/v = 10:1, 3 × 10 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 100:1) to give 3aa (0.11 g, 0.41 mmol, 82%) as a colorless oil. All the resonances in 1H NMR and 13C NMR spectra were consistent with the reported values in the literature: