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. Author manuscript; available in PMC: 2012 Oct 19.
Published in final edited form as: J Am Chem Soc. 2011 Sep 27;133(41):16330–16333. doi: 10.1021/ja2082087

Table 1.

Screening of Ligands and Electrophiles for Ni-catalyzed Asymmetric α-Arylation of 2-Methyl-1-indanone.a

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entry PhX Ligand yield (%) ee (%) entry PhX Ligand yield (%) ee (%)
1 PhBr L1 61 76 7 PhI L1 36 37
2 PhBr L2 40 47 8 PhOTf L1 33 70
3 PhBr L3 53 50 9 PhCl L1 78 93
4 PhBr L4 44 42 10 PhCl L3 67 94
5 PhBr L5 55 60 11 PhCl L5 77 96
6 PhBr L6 59 60 12 PhCl L6 80 94
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a

Conditions: 2-Methyl-1-indanone (0.200 mmol), PhX (0.400 mmol), NaOtBu (0.400 mmol), Ni(COD)2 (0.010 mmol), and Ligand (0.012 mmol); solvent: toluene (1.0 mL); temperature: 80 °C; ee was determined by chiral HPLC analysis.