Skip to main content
. 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 4.

Room-Temperature Asymmetric α-Arylation of Ketones with Chloro- and Bromoarenes Catalyzed by [(R)-BINAP]Ni(η2-NC-Ph)a

graphic file with name nihms328258u4.jpg
1 graphic file with name nihms328258t38.jpg
X = Cl (10%)
yield: 91%; ee: >99%
X = Br (5%)
yield: 95%; ee: >99%		 2 graphic file with name nihms328258t39.jpg
X = Cl (10%)
yield: 64%; ee: 98%
X = Br (5%)
yield: 74%; ee: 99%		 3 graphic file with name nihms328258t40.jpg
X = Cl (10%)
yield: 93%; ee: >99%
X = Br (5%)
yield: 61%; ee: 97%
4 graphic file with name nihms328258t41.jpg
X = Cl (5%)
yield: 92%; ee: >99%
X= Br (5%)
yield: 96%; ee: >99%		 5 graphic file with name nihms328258t42.jpg
X = Cl (10%)
yield: 72%; ee: >99%
X = Br (5%)
yield: 50%; ee: 98%		 6 graphic file with name nihms328258t43.jpg
X = Cl (10%)
yield: 59%; ee: 95%
X = Br (10%)
yield: 74%; ee: 83%
a

Conditions: Ketones (0.200 mmol), ArX (0.400 mmol), NaOtBu (0.400 mmol), and [(R)-BINAP]Ni(η2-NC-Ph) (0.010 mmol, 5% or 0.020 mmol, 10%); solvent: toluene (1.0 mL); ee was determined by chiral HPLC analysis.