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A rapid and convenient approach to functionally diverse monofluorinated vinylic compounds

✍ Scribed by Jonathan M. Percy; Robin D. Wilkes

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
904 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Monofluorinated allylic ether 3, synthesised in 4 steps from trifluoroethanol, underwent metallation at the CF vinylic position upon treatment with strong base. Monofluoro vinyllithium 4 was trapped efficiently with a variety of electrophiles, including Group (IV) halides, methyl iodide and benzaldehyde. Attempts to couple monofluoro vinyl stannane 5d with aryl iodides and triflates under palladium catalysis proved only moderately successful. Conversion of 4 to the monofluoro vinylzinc reagent allowed access to monofluoro vinyl iodide 5e, which was successfully coupled with a range of terminal alkynes.

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