Synthesis and characterization of β-haloalkenyl-λ3- bromanes: Stereoselective markovnikov addition of difluoro(aryl)- λ3-bromane to terminal acetylenes

Masahito Ochiai, Yoshio Nishi, Takeshi Mori, Norihiro Tada, Takashi Suefuji, Hermann J. Frohn

研究成果: ジャーナルへの寄稿学術誌査読

26 被引用数 (Scopus)

抄録

Reported here for the first time are the synthesis, isolation, and characterization of hypervalent β-haloalkenyl-λ3-bromanes. Exposure of terminal alkynes to p-trifluoromethylphenyl(difluoro)-λ3-bromane activated by BF3-i-Pr2O resulted in fluoro-λ3-bromanation of the triple bonds in a Markovnikov fashion, yielding (E)-β-fluoroalkenyl-λ3-bromanes stereoselectively in good yields. 5-Chloro-1-pentynes undergo domino λ3-bromanation-chlorine shift-fluorination or λ3-bromanation-chlorine shift-alkyl shift-fluorination reaction, depending on the substituents and afford (E)-β-chloroalkenyl-λ3-bromanes stereoselectively in high yields. The β-chloroalkenyl-λ3-bromanes contain three kinds of halogen atoms, F, Cl, and Br, in the molecule.

本文言語英語
ページ(範囲)10460-10461
ページ数2
ジャーナルJournal of the American Chemical Society
127
30
DOI
出版ステータス出版済み - 8月 3 2005
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学一般
  • 生化学
  • コロイド化学および表面化学

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