(untitled) - Yasukawa, T; Miyamura, H; Kobayashi, S (Org. Biomol. Chem., 2011)
Alkynylation of 1a with 2a – Representative ProcedureAn oven-dried Schlenk tube was charged with diphenyl sulfoxide (1a, 61 mg, 0.30 mmol), 1-dodecyne (2a, 60 mg, 0.36 mmol), Pd–PEPPSI–SIPr (5.1 mg, 0.0075 mmol), LiOtBu (36 mg, 0.45 mmol), and THF (1.5 mL). The resulting mixture was stirred at 70 °C for 6 h. The reaction was quenched with sat. aq NH4Cl (0.10 mL), and the resulting mixture was passed through pads of anhydrous Na2SO4, activated alumina, and silica gel with Et2O as an eluent. The ethereal solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with an eluent (hexane/toluene = 25:1) to provide 3aa as a colorless oil (68 mg, 0.28 mmol, 93% yield). All the resonances in 1H NMR and 13C NMR spectra were consistent with reported values. See: