%0 Generic %A Liang, Yufan %A Fu, Gregory C. %D 2015 %T Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones %U https://acs.figshare.com/articles/dataset/Catalytic_Asymmetric_Synthesis_of_Tertiary_Alkyl_Fluorides_Negishi_Cross_Couplings_of_Racemic_Dihaloketones/2031360 %R 10.1021/ja501815p.s004 %2 https://acs.figshare.com/ndownloader/files/3602670 %K electrophile %K presence %K DihaloketonesThe %K Racemic %K geminal dihalides %K enantioenriched %K array %K Negishi reactions %K discipline %K variety %K Tertiary Alkyl Fluorides %K racemic %K Article %K enantioselective synthesis %K approach %K method %K Catalytic Asymmetric Synthesis %K stereoconvergent %K fluoroketone %K molecule %K construction %K catalyst %K alkyl fluorides %K halo %K organofluorine compounds %K aid %K bond %X 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 α-halo-α-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 α-fluoroketones, can be converted into an array of interesting organofluorine compounds. %I ACS Publications