Reaction of triarylbismuth difluorides 1 with allyltrimethylsilane 2 in CH2Cl2 in the presence of BF3·OEt2 at low temperature generatesallyltriarylbismuthoniumcompound 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
Umpolung of reactivity of allylsilane, allylgermane, and allylstannane via their reaction with thallium (III) salt: a new allylation reaction for aromatic compound
作者:Masahito Ochiai、Masao Arimoto、Eiichi Fujita
DOI:10.1016/s0040-4039(01)93023-0
日期:1981.1
A new direct allylation of the aromatic compound has been developed. A combination of allylsilane, allylgermane, or allylstannane and thallium (III) trifluoroacetate gave rise to an allyl cationic species which was allowed to react with an aromatic compound, a nucleophile, to give allylation product(s) in good yields.
Umpolung of reactivity of allylsilane, allylgermane, and allylstannane via their reaction with thallium (III) salt: A new allylation reaction for aromatic compounds.
A new direct allylation of aromatic compounds has been developed. A mixture of allylsilane, allylgermane, or allylstannane and thallium (III) trifluoroacetate was allowed to react with an aromatic compound, a nucleophile, to give allylation product (s) in good yields via an allylcationic species. Thus, the usefulness of these allylmetal compounds as allyl cation equivalents was established.