allylic C−C σ‐bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2‐Aryl or alkyl migration through allylic C−C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O‐atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal‐free
The catalytic Friedel–Crafts alkylation reaction of aromatic compounds with benzyl or allyl silyl ethers using Cl2Si(OTf)2 or Hf(OTf)4
作者:Isamu Shiina、Masahiko Suzuki
DOI:10.1016/s0040-4039(02)01376-x
日期:2002.9
The Friedel-Crafts alkylation reaction of various aromatic compounds with benzyl or allyl silyl ethers is effectively promoted under mild reaction conditions using Lewis acid catalysts. A mixture of the desired phenyltolylmethanes is obtained in 80% yield from toluene with benzyl dimethylsilyl or trimethylsilyl ether at 50degreesC in the presence of a catalytic amount of Cl2Si(OTf)(2) or Hf(OTf)(2). (C) 2002 Elsevier Science Ltd. All rights reserved.
Smith, Keith; Pollaud, Guy M, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3519 - 3520