Simple Synthesis of Fluorinated Ene-Ynes via In Situ Generation of Allenes
Keyword(s):
AbstractFluorination of small molecules is a key route toward modulating reactivity and bioactivity. The 1,3 ene-yne functionality is an important synthon towards complex products, as well as a common functionality in biologically active molecules. Here, we present a new synthetic route towards fluorinated ene-ynes from simple starting materials. We employ gas chromatography-mass spectrometry analysis to probe the sequential eliminations necessary for this transformation and observe an allene intermediate. The ene-yne products are sufficiently fluorous to enable purification via fluorous extraction. This methodology will allow facile access to functional, fluorous ene-ynes.
2019 ◽
Vol 1599
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pp. 17-24
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2010 ◽
Vol 44
(10)
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pp. 1301-1307
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2006 ◽
2016 ◽
Vol 18
(4)
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pp. 365-369
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