Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 14, Pages 5520-5524Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja501815p
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Funding
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- NSF CRIF:MU award [CHE-0639094]
- Gordon and Betty Moore Foundation
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The development of new approaches to the construction of fluorine-containing target molecules is important for a variety of scientific disciplines, including medicinal chemistry. In this Article, we describe a method for the catalytic enantioselective synthesis of tertiary alkyl fluorides through Negishi reactions of racemic alpha-halo-alpha-fluoroketones, which represents the first catalytic asymmetric cross-coupling that employs geminal dihalides as electrophiles. Thus, selective reaction of a C-Br (or C-Cl) bond in the presence of a C-F bond can be achieved with the aid of a nickel/bis(oxazoline) catalyst. The products of the stereoconvergent cross-couplings, enantioenriched tertiary alpha-fluoroketones, can be converted into an array of interesting organofluorine compounds.
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