Potassium Phosphate, Tribasic → 4-(Prop-1-en-2-yl)dibenzo[b,d]furan

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4-Iododibenzo[b,d]furan (25 g, 85.0 mmol) and potassium phosphate (58.7 g, 255 mmol) were dissolved in 500 mL of toluene and 50 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (15.98 mL, 85 mmol), Pd2(dba)3 (1.55 g, 1.7 mmol) and S-Phos (2.79 g, 6.8 mmol) were added. The reaction was refluxed for 18 hours. After cooling the reaction to room temperature, 100 mL of water was added, the organic and aqueous layers were separated, and the aqueous layer was extracted twice with 100 mL of ethyl acetate. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 3% ethyl acetate in hexane to 5% ethyl acetate in hexane, v/v) to yield 14.5 g (82%) of pure product.

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