Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles

Ming Chang P. Yeh, Chia Jung Liang, Tzu Lin Huang, Hsiao Ju Hsu, Yu Shuo Tsau

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl- protected N-containing cyclic enynols using inexpensive BF3· OEt2 is described. In this reaction, BF3 reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp2)-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.

Original languageEnglish
Pages (from-to)5521-5529
Number of pages9
JournalJournal of Organic Chemistry
Volume78
Issue number11
DOIs
Publication statusPublished - 2013 Jun 28

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Lewis Acids
Fluorination
Halogenation
Cyclization
Fluorides
Skeleton
Transition metals
Nitrogen
Metals
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols : Synthesis of fluorinated azabicycles. / Yeh, Ming Chang P.; Liang, Chia Jung; Huang, Tzu Lin; Hsu, Hsiao Ju; Tsau, Yu Shuo.

In: Journal of Organic Chemistry, Vol. 78, No. 11, 28.06.2013, p. 5521-5529.

Research output: Contribution to journalArticle

Yeh, Ming Chang P. ; Liang, Chia Jung ; Huang, Tzu Lin ; Hsu, Hsiao Ju ; Tsau, Yu Shuo. / Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols : Synthesis of fluorinated azabicycles. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 11. pp. 5521-5529.
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