trans-beta-Bromostyrene → trans-Stilbene

Participants

Reaction Steps

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.

Provenance & Evidence