Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

Zhu, Wei; Xu, Tingyi; Han, Wen‐Yong

doi:10.6023/cjoc202009055

Chinese Journal of Organic Chemistry

2021

DOI: 10.6023/cjoc202009055

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Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

Wei Zhu¹,

Tingyi Xu²,

Wen‐Yong Han³

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Cited by 3 publications

References 44 publications

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Synthesis of Difluoromethyl Pyrazolines and Pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with Electron‐deficient Olefins

Ren

Feng

et al. 2022

Asian J Org Chem

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Difluoroacetohydrazonoyl bromides, which are stable in air at room temperature, are demonstrated to be good difluoromethyl building blocks for construction of CF2H‐substituted pyrazoline and pyrazole compounds via [3+2] cycloaddition with electron‐deficient olefins under mild conditions. A series of CF2H‐substituted pyrazolines and pyrazoles were obtained in good yields. The method has the advantages of mild reaction conditions, good regioselectivity, broad substrate scopes and easy operation.

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Synthesis of Difluoromethyl Pyrazolines and Pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with Electron‐deficient Olefins

Ren

Feng

et al. 2022

Asian J Org Chem

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Group VIII metal difluorocarbene complexes: Synthesis and applications

Ding,

Yao,

Lin

et al. 2024

Journal of Fluorine Chemistry

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Copper-Catalyzed Radical Addition of Alkynols to Synthesize Difluoroheterocyclic Compounds

et al. 2023

Org. Lett.

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A convenient method for the synthesis of fluorine-containing heterocyclic compounds was developed by a copper-catalyzed free radical addition reaction of alkynol and ethyl bromodifluoroacetate. This strategy involves copper-catalyzed free radical addition and molecular lactone exchange of ethynyl alcohol and ethyl bromodifluoroacetate. The method is characterized by easy availability of raw materials, good stereochemical selectivity, and simple operation. More importantly, valuable tetrasubstituted E-configurated alkenes and various vinyl C–Br bonds and difluoromethylene-containing functionalized heterocycles can be obtained by this method.

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Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

Cited by 3 publications

References 44 publications

Synthesis of Difluoromethyl Pyrazolines and Pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with Electron‐deficient Olefins

Synthesis of Difluoromethyl Pyrazolines and Pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with Electron‐deficient Olefins

Group VIII metal difluorocarbene complexes: Synthesis and applications

Copper-Catalyzed Radical Addition of Alkynols to Synthesize Difluoroheterocyclic Compounds

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