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Synfacts 2015; 11(10): 1077
DOI: 10.1055/s-0035-1560233
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Arylation of Secondary Alkyl Electrophiles

Contributor(s):
Hisashi Yamamoto
,
Ramesh C. Samanta
Liang Y, Fu GC * California Institute of Technology, Pasadena, USA
Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group.

J. Am. Chem. Soc. 2015;
137: 9523-9526
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Further Information

Publication History

Publication Date:
18 September 2015 (online)

 
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Key words

bis(oxazoline)s - Negishi arylation - nickel

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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