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. 2015 Jun 5;17(11):2567-9.
doi: 10.1021/acs.orglett.5b00979. Epub 2015 May 20.

Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines

Shuming Chen  1 , Robert G Bergman  2 , Jonathan A Ellman  1
Affiliations

Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines

Shuming Chen et al. Org Lett. .

Abstract

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.

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Figures

Scheme 1
Scheme 1
Scope of Rh(III)-catalyzed fluoropyridine formation from oximes and internal alkynesa a All reactions were set up in air on bench-top. Yields are based upon the mass balance of pure material after column chromatography.
Scheme 2
Scheme 2
Scope of Rh(III)-catalyzed fluoropyridine formation from oximes and terminal alkynesa a All reactions were set up in air on the bench-top. Yields are based upon the mass balance of pure material after column chromatography.
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References

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