Difluoro-λ3-bromane-induced oxidative carbon-carbon bond-forming reactions: Ethanol as an electrophilic partner and alkynes as nucleophiles

Masahito Ochiai, Akira Yoshimura, Takeshi Mori, Yoshio Nishi, Masaya Hirobe

研究成果: ジャーナルへの寄稿学術誌査読

30 被引用数 (Scopus)

抄録

Reported here for the first time are the oxidative couplings of alkynes and primary alcohols yielding conjugated enones. Although the BF3-catalyzed reaction of terminal alkynes with p-trifluoromethylphenyl(difluoro)-λ3-bromane results in the fluoro-λ3-bromanation of triple bonds to afford (E)-β-fluorovinyl-λ3-bromanes, reaction of an alkyne with the difluoro-λ3-bromane in the presence of an alcohol and BF3-Et2O affords directly conjugated enones in good yields. The reaction proceeds in a highly stereo- and regioselective manner under metal-free conditions. Interestingly, no formation of enones was detected, when difluoro-λ3-iodane p-CF3C6H4IF2 was used instead of the λ3-bromane. A mechanism involving a λ3-bromane-induced oxidation of an alcohol to an aldehyde, [2 + 2] cyclization with alkynes yielding 2H-oxetes, and finally the electrocyclic ring opening is discussed.

本文言語英語
ページ(範囲)3742-3743
ページ数2
ジャーナルJournal of the American Chemical Society
130
12
DOI
出版ステータス出版済み - 3月 26 2008
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

フィンガープリント

「Difluoro-λ3-bromane-induced oxidative carbon-carbon bond-forming reactions: Ethanol as an electrophilic partner and alkynes as nucleophiles」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル