Electrophilic allylation of arenes with in situ generated allyltriarylbismuthonium compound: The Bismuth-mediated polarity inversion of allylsilanes

Article abstract of DOI:10.1016/0040-4039(95)01600-7

Reaction of triarylbismuth difluorides 1 with allyltrimethylsilane 2 in CH₂Cl₂ in the presence of BF₃·OEt₂ at low temperature generates allyltriarylbismuthonium compound 3 as a pale yellow solution, in which aromatic hydrocarbons and ethers, triphenylphosphine, dimethyl sulfide, p-toluenesulfinate, and thiophenol are all readily allylated to afford the corresponding allyl derivatives in moderate to good yields.