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Org Lett. 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.

Author information

1
†Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
2
‡Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California-Berkeley, Berkeley, California 94720, United States.

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.

PMID:
25992591
PMCID:
PMC4477688
DOI:
10.1021/acs.orglett.5b00979
[Indexed for MEDLINE]
Free PMC Article

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