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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Oct 28;135(44):10.1021/ja408561b. doi: 10.1021/ja408561b

Table 3.

Catalytic Asymmetric Synthesis of 1,1-Diarylalkanes from Racemic Benzylic Alcohols: Scope with Respect to the Nucleophilea

graphic file with name nihms535721u4.jpg
entry Ar1 ee (%) yield (%)b
1 graphic file with name nihms535721t19.jpg X = H 94 96
2c Me 93 91
3 F 94 95
4 Cl 94 95
5 Br 94 87
6c I 94 66
7 CF3 94 98
8d CO2Et 93 91
9d CN 92 83

10 graphic file with name nihms535721t20.jpg X = CF3 94 96
11d CO2Et 93 92

12 graphic file with name nihms535721t21.jpg 93 87
13e graphic file with name nihms535721t22.jpg 92 93
14d graphic file with name nihms535721t23.jpg 94 87
15d graphic file with name nihms535721t24.jpg 93 77
a

All data are the average of two experiments.

b

Yield of purified product.

c

Equivalents of arylzinc reagent: 1.5.

d

Benzylic alcohol coupling partner: 1-phenylpropanol.

e

Reaction temperature: −30 °C.