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Typical Procedure for the Sila-Sonogashira Cross-Coupling Reactions of Aryl Chlorides 2 with Alkynylsilanes 1 To a solution of Pd(OAc)2 (45 mg, 0.2 mmol, 10 mol, and, )-DIOP (100 mg, 0.2 mmol, 10 mol, in dry DMF (8 mL) were added 1-(4-methoxypheny)-2-trimethylsilylethyne (1b, 519 μL, 2.4 mmol, 4-cyanophenyl chloride (2b, 275 mg, 2 mmol, and CuCl (20 mg, 0.2 mmol, 10 mol, at r.t. The dark red suspension was heated for 12 h at 120°C and monitored by GC and TLC. After completion of the reaction, the reaction mixture was quenched with 1 M HCl and extracted with Et2O (3 x 20 mL, The combined organics were washed with brine and dried over anhydrous MgSO4. Filtration and concentration with a rotary evaporator gave a viscous oil. The residue was purified by flash column chromatography on SiO 2 (hexane-Et2O, 8:2, Rf, 0.39, 3h 331 mg, 1.42 mmol, 71, was obtained as a white solid
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3): δ = 3.84 (s, 3 H), 6.89-6.92 (m, 2 H), 7.47-7.50 (m, 2 H), 7.56-7.64 (m, 4 H).
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