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7.6.11.2.5 Variation 5: Nickel-Catalyzed Enantioselective Coupling of Grignard Reagents with Aryl Compounds

DOI: 10.1055/sos-SD-007-00562

Takahashi, T.; Liu, Y.Science of Synthesis, (20047602.

For the coupling reaction of 2-methyl-1-naphthylmagnesium bromide with 1-bromo-2-methylnaphthalene to give 2,2-dimethyl-1,1-binaphthyl (13), nickel catalysts with monodentate phosphine ligands are more active than those with bidentate ligands. When (S)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyl methyl ether (14) is used as the ligand at 15°C for 92hours, (R)-13 is obtained in 69% yield with an improved enantiomeric excess of 95% (Scheme 10).[‌56‌]

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