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Synfacts 2009(3): 0285-0285  
DOI: 10.1055/s-0028-1087782
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Nickel-Catalyzed Cross-Coupling of α-Bromoketones with Arylzinc Reagents

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
P. M. Lundin, J. Esquivias, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

This paper described the NiCl2˙glyme/(+)-ligand catalyzed cross-coupling reaction of arylzinc with racemic secondary α-bromoketones. The resulting α-aryl ketones were obtained in excellent yields and good to excellent enantioselectivities. Remarkably, the unusually mild reaction conditions (-30 ˚C and no activators) allowed the generation of potentially labile tertiary stereocenters.