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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 3.

Asymmetric Heteroarylation of Ketones with Heteroaryl Halides Catalyzed by Ni(COD)2/(R)-DIFLUORPHOSa

graphic file with name nihms328258u3.jpg
entry ArX yield (%) ee (%)
n = 0
1 graphic file with name nihms328258t22.jpg X = Br 69 57
2 X = Cl 93 97
3 graphic file with name nihms328258t23.jpg 54 91
4 graphic file with name nihms328258t24.jpg R = OMe 75 41
5 R = Me 87 94
6 graphic file with name nihms328258t25.jpg R′ = CF3 85 81
7 R′ = F 86 98
8 R′ = CN 87 21
9 graphic file with name nihms328258t26.jpg 76 96
10 graphic file with name nihms328258t27.jpg 54 95
11 graphic file with name nihms328258t28.jpg 90 99
12 graphic file with name nihms328258t29.jpg 85 90
n = 1
13 graphic file with name nihms328258t30.jpg X = Br 73 55
14 X = Cl 89 99
15 graphic file with name nihms328258t31.jpg 68 94
16 graphic file with name nihms328258t32.jpg R = OMe 72 35
17 R = Me 86 98
18 graphic file with name nihms328258t33.jpg R′ = CF3 85 96
19 R′ = F 89 99
20 R′ = CF3 84 93
21 graphic file with name nihms328258t34.jpg 54 96
22 graphic file with name nihms328258t35.jpg 45 97
23 graphic file with name nihms328258t36.jpg 87 99
24 graphic file with name nihms328258t37.jpg 79 92
a

Conditions: Indanones or tetralones (0.200 mmol), chloro- or bromoarenes (0.400 mmol), NaOtBu (0.400 mmol), Ni(COD)2 (0.020 mmol), and (R)-DIFLUORPHOS (0.024 mmol); solvent: toluene (1.0 mL); temperature: 70 °C; reaction time: 28 h; ee was determined by chiral HPLC analysis.