Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 39, Pages 6236-6244Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001071
Keywords
Fluorine; Heterocycles; HFO-1234yf; Trifluoromethyl; Ynones
Categories
Funding
- GlaxoSmithKline
- EPSRC
- Durham University MChem programme
- EPSRC [1915208] Funding Source: UKRI
Ask authors/readers for more resources
Reaction of low cost, readily available 4(th)generation refrigerant gas 2,3,3,3-tetrafluoropropene (HFO-1234yf) with lithium diisopropylamide (LDA) leads to formation of lithium 3,3,3-trifluoropropynide, addition of which to a range of aldehydes formed CF3-alkynyl alcohol derivatives on multigram scale, which were oxidised using Dess-Martin periodinane (DMP) to give substituted CF3-ynones with minimal purification required. Michael-type additions of alcohol and amine nucleophiles to CF3-ynones are rapid and selective, affording a range of CF3-enone ethers and enaminones in excellent yields with high stereoselectivity for theZ-isomer. By analogous reactions with difunctional nucleophiles, a wide range of CF3-substituted pharmaceutically relevant heterocyclic structures can be accessed, exemplified in the simple synthesis of the anti-arthritis drug celecoxib from HFO-1234yf in just three steps.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available