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

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19 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)10460-10461
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number30
DOIs
Publication statusPublished - Aug 3 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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