[(E)-2-bromoethenyl]benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: FC-72 (10 mL) was charged to the U-tube (F-phase), a solution of (E)-bromostyrene (130 μL, 1.0 mmol) in MeCN (1 mL) was charged to the S-phase of the U-tube and a solution of Pd(PPh3)4 (23 mg, 0.02 mmol) in toluene (1.5 mL) was charged to the P-phase of the U-tube. After PhZnI (0.5 M in THF, 1.0 mL) was added to the P-phase, each phase was stirred for 1 day. The mixture in the P-phase was decanted into water, extracted with ether, dried over MgSO4 and then evaporated. However, trans-stilbene was not obtained in the P-phase and (E)-bromostyrene was recovered from the S-phase. The mixture in the P-phase was decanted into water extracted with ether dried over MgSO4 evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an illustrative example, a coupling reaction was conducted between (E)-2-bromostyrene (PhCH═CHBr) and phenylzinc iodide (PhZnI) promoted by a fluorous palladium catalyst. The catalyst was prepared from Pd2(dba)3 and the known fluorous phosphine (p-C6F13CH2CH2C6H4)3P. A mixture of the catalyst in FC-72 was contacted in a U-tube with a first organic phase containing (E)-2-bromostyrene in acetonitrile and a second organic phase containing phenylzinc iodide in THF. After one day at ambient temperature, each organic phase was removed and subjected to standard aqueous workup. Unreacted (E)-2-bromostyrene was recovered from the first organic phase while the coupled reaction product, (E)-stilbene (PhCH═CHPh) was isolated from the second organic phase. each organic phase was removed was recovered from the first organic phase while the coupled reaction product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cuprous iodide (0.4 g, 2.1 mmol) and bis-triphenylphosphine palladium (II) chloride (0.8 g, 1.14 mmol) were added to a solution of pent-4-yn-1-ol (16 g, 193 mmol) (Jones, Eglinton, and Whiting, Org. Syn. Coll., 4, 755, (1963)) and E-styryl bromide (34.34 g, 188 mmol) (Feuerstein and Heimann, Ber., 34, 1468 (1901)) in anhydrous diethylamine (250 ml). The whole was stirred under an atmosphere of dry nitrogen with the exclusion of moisture and light for 16 hours. The diethylamine was removed at reduced pressure and the residue diluted with water (500 ml). The aqueous mixture was extracted with ether. The ethereal extracts were passed down a column composed of silica (100 g), Celite (trade name, from Koch-light Ltd) (100 g) and activated charcoal (20 g) at 3 psi (21 KPa) pressure. The column was washed with ether (200 ml) and the combined organic extracts dried over anhydrous magnesium sulphate. Removal of solvents gave 30.5 g of 7-phenyl-hept-4-yn-6E-en-1-ol as a pale brown oil. The material was not purified further. The diethylamine was removed at reduced pressure the residue diluted with water (500 ml) The aqueous mixture was extracted with ether The column was washed with ether (200 ml) the combined organic extracts dried over anhydrous magnesium sulphate Removal of solvents

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cuprous iodide (0.4 g, 2.1 mmol) and bis-triphenylphosphine palladium (II) chloride (0.8 g, 1.14 mmol) were added to a solution of pent-4-yn-1-ol (16 g, 193 mmol) (Jones, Eglinton, and Whiting, Org. Syn. Coll., 4, 755, (1963)) and E-styryl bromide (34.34 g, 188 mmol) (Feurerstein and Heimann, Ber., 34, 1468 (1901)) in anhydrous diethylamine (250 m). The whole was stirred under an atmosphere of dry nitrogen with the exclusion of moisture and light for 16 hours. The diethylamine was removed at reduced pressure and the residue diluted with water (500 ml). The aqueous mixture was extracted with ether. The ethereal extracts were passed down a column composed of silica (100 g), Celite (trade name, from Koch-light Ltd) (100 g) and activated charcoal (20 g) at 3 psi (21 KPa) pressure. The column was washed with ether (200 ml) and the combined organic extracts dried over anhydrous magensium sulphate. Removal of solvents gave 30.5 g of 7-phenyl-hept-4-yn-6E-en-1-ol as a pale brown oil. The material was not purified further. The diethylamine was removed at reduced pressure the residue diluted with water (500 ml) The aqueous mixture was extracted with ether The column was washed with ether (200 ml) the combined organic extracts dried over anhydrous magensium sulphate Removal of solvents

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: FC-72 (10 mL) was charged to the U-tube (F-phase), a solution of (E)-bromostyrene (130 μL, 1.0 mmol) in MeCN (1 mL) was charged to the S-phase of the U-tube and a solution of Pd(PPh3)4 (23 mg, 0.02 mmol) in toluene (1.5 mL) was charged to the P-phase of the U-tube. After PhZnI (0.5 M in THF, 1.0 mL) was added to the P-phase, each phase was stirred for 1 day. The mixture in the P-phase was decanted into water, extracted with ether, dried over MgSO4 and then evaporated. However, trans-stilbene was not obtained in the P-phase and (E)-bromostyrene was recovered from the S-phase. The mixture in the P-phase was decanted into water extracted with ether dried over MgSO4 evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an illustrative example, a coupling reaction was conducted between (E)-2-bromostyrene (PhCH═CHBr) and phenylzinc iodide (PhZnI) promoted by a fluorous palladium catalyst. The catalyst was prepared from Pd2(dba)3 and the known fluorous phosphine (p-C6F13CH2CH2C6H4)3P. A mixture of the catalyst in FC-72 was contacted in a U-tube with a first organic phase containing (E)-2-bromostyrene in acetonitrile and a second organic phase containing phenylzinc iodide in THF. After one day at ambient temperature, each organic phase was removed and subjected to standard aqueous workup. Unreacted (E)-2-bromostyrene was recovered from the first organic phase while the coupled reaction product, (E)-stilbene (PhCH═CHPh) was isolated from the second organic phase. each organic phase was removed was recovered from the first organic phase while the coupled reaction product