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Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines
- Chen, Shuming, Bergman, Robert
G., Ellman, Jonathan A.
- Organic letters 2015 v.17 no.11 pp. 2567-2569
- air, alkynes, carbon-hydrogen bond activation, chemical reactions, oximes, positional isomers, pyridines, regioselectivity
- A Rh(III)-catalyzed C–H functionalization approach was developed for the preparation of multisubstituted 3-fluoropyridines from α-fluoro-α,β-unsaturated oximes and alkynes. Oximes substituted with aryl, heteroaryl, and alkyl β-substituents were effective coupling partners, as were symmetrical and unsymmetrical alkynes with aryl and alkyl substituents. The first examples of coupling α,β-unsaturated oximes with terminal alkynes was also demonstrated and proceeded with uniformly high regioselectivity to provide single 3-fluoropyridine regioisomers. Reactions were also conveniently set up in air on the benchtop.