Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 11, Pages 5521-5529Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400634c
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Funding
- National Science Council [NSC 98-2119-M-003-004-MY3, NSC 101-2113-M-003-002-MY3]
- National Taiwan Normal University
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The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl-protected N-containing cyclic enynols using inexpensive BF3 center dot 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(sp(2))-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.
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