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

22 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

ASJC Scopus subject areas

  • Organic Chemistry

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