Regioselective Nickel‐Catalyzed Hydroarylation of <i>gem</i>‐Difluoroalkenes for the Synthesis of the ArCF2−${\rm{ArCF}}_{{2}^{-}}$ Moiety

The incorporation of fluorine and fluorinated functional groups into organic molecules alters their physicochemical properties, thereby facilitating the advancement of novel therapeutics, agricultural chemicals, biological probes, and materials. Nevertheless, there remains a deficiency of methodologies for the catalytic synthesis of certain significant fluorine-containing groups, such as <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"> <mml:semantics><mml:msub><mml:mi>ArCF</mml:mi> <mml:msup><mml:mn>2</mml:mn> <mml:mo>-</mml:mo></mml:msup> </mml:msub> <mml:annotation>${\rm{ArCF}}_{{2}^{-}}$</mml:annotation></mml:semantics> </mml:math> , under mild conditions utilizing earth-abundant metals. Herein, we report a method for the regioselective hydroarylation of gem-difluoroalkenes under mild conditions with the aid of Ni─H intermediate catalysis, which is capable of efficiently synthesizing compounds containing the <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"> <mml:semantics><mml:msub><mml:mi>ArCF</mml:mi> <mml:msup><mml:mn>2</mml:mn> <mml:mo>-</mml:mo></mml:msup> </mml:msub> <mml:annotation>${\rm{ArCF}}_{{2}^{-}}$</mml:annotation></mml:semantics> </mml:math> structural motifs and possesses good functional group tolerance.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-03-31
DOI
https://doi.org/10.1002/anie.202424714
Citations
9
Primary Topic
Fluorine in Organic Chemistry
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article
Field-Weighted Citation Impact
7.12
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article

Regioselective Nickel‐Catalyzed Hydroarylation of gem‐Difluoroalkenes for the Synthesis of the ArCF2−${\rm{ArCF}}_{{2}^{-}}$ Moiety

Yaxing Wu, Ruitong Zhang, Xiangyu Chen, Chao Chen et al.
9 citations
Angewandte Chemie International Edition
Fluorine in Organic Chemistry
7.12
article

Regioselective Nickel‐Catalyzed Hydroarylation of gem‐Difluoroalkenes for the Synthesis of the ArCF2−${\rm{ArCF}}_{{2}^{-}}$ Moiety

Yaxing Wu, Ruitong Zhang, Xiangyu Chen, Chao Chen, Fei Wang
article en
9 citations

Abstract

The incorporation of fluorine and fluorinated functional groups into organic molecules alters their physicochemical properties, thereby facilitating the advancement of novel therapeutics, agricultural chemicals, biological probes, and materials. Nevertheless, there remains a deficiency of methodologies for the catalytic synthesis of certain significant fluorine-containing groups, such as <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"> <mml:semantics><mml:msub><mml:mi>ArCF</mml:mi> <mml:msup><mml:mn>2</mml:mn> <mml:mo>-</mml:mo></mml:msup> </mml:msub> <mml:annotation>${\rm{ArCF}}_{{2}^{-}}$</mml:annotation></mml:semantics> </mml:math> , under mild conditions utilizing earth-abundant metals. Herein, we report a method for the regioselective hydroarylation of gem-difluoroalkenes under mild conditions with the aid of Ni─H intermediate catalysis, which is capable of efficiently synthesizing compounds containing the <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"> <mml:semantics><mml:msub><mml:mi>ArCF</mml:mi> <mml:msup><mml:mn>2</mml:mn> <mml:mo>-</mml:mo></mml:msup> </mml:msub> <mml:annotation>${\rm{ArCF}}_{{2}^{-}}$</mml:annotation></mml:semantics> </mml:math> structural motifs and possesses good functional group tolerance.

Angewandte Chemie International EditionVol. 64(23)
Tsinghua University (CN)
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Openalex Percentile: Top 3%
Fluorine in Organic Chemistry
7.12
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Regioselective Nickel‐Catalyzed Hydroarylation of <i>gem</i>‐Difluoroalkenes for the Synthesis of the ArCF2−${\rm{ArCF}}_{{2}^{-}}$ Moiety — Yaxing Wu, Ruitong Zhang, et al. · Angewandte Chemie International Edition (2025) | TGRS Research Map | TGRS