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Issue 40, 2019
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Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides

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Abstract

A nickel-catalyzed difluoroalkylation of α-C–H bonds of aryl ketones to furnish highly stereo-defined tetrasubstituted monofluoroalkenes or quaternary alkyl difluorides from secondary or tertiary ketones, respectively, has been established. Mechanistic investigations indicated that these C–H fluoroalkylations proceed via a Ni(I)/Ni(III) catalytic cycle. An obvious fluorine effect was observed in the reaction, and this reaction has demonstrated high stereoselectivity, mild conditions, and broad substrate scopes, thus enabling the late-stage fluoroalkylation of bioactive molecules. This method offers a solution for expedient construction of monofluoroalkenes from readily available materials, and provides an efficient approach for the synthesis of bioactive fluorinated compounds for the discovery of lead compounds in medicinal chemistry.

Graphical abstract: Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides

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Publication details

The article was received on 10 Jun 2019, accepted on 17 Aug 2019 and first published on 20 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC02806D
Chem. Sci., 2019,10, 9285-9291
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides

    C. Li, Y. Cao, R. Jin, K. Bian, Z. Qin, Q. Lan and X. Wang, Chem. Sci., 2019, 10, 9285
    DOI: 10.1039/C9SC02806D

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