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DOI: 10.1055/s-0035-1560233
Asymmetric Arylation of Secondary Alkyl Electrophiles
Publication History
Publication Date:
18 September 2015 (online)
![](https://www.thieme-connect.de/media/synfacts/201510/i_h117_s1_10-1055_s-0035-1560233.gif)
Significance
Enantiodivergent cross-coupling of an arylzinc reagent and a secondary alkyl halide with a trifluormethyl substituent was achieved by using a readily available nickel/bis(oxazoline) catalyst. The fluorinated products were obtained in good yields and with high enantioselectivities.
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Comment
Fu and co-workers have previously reported an enantiodivergent cross-coupling of a racemic secondary electrophile by using a chiral nickel catalyst (J. Am. Chem. Soc. 2005, 127, 4594; J. Am. Chem. Soc. 2014, 136, 12161). The chiral catalyst can differentiate between a trifluoromethyl and an alkyl group to deliver the cross-coupling product with high enantioselectivity. The cross-coupling reaction is not air-sensitive, as identical results were obtained when the reaction was conducted in the presence of air.
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![](https://www.thieme-connect.de/media/synfacts/201510/i_h117_s1_10-1055_s-0035-1560233.gif)