ArticleNature communications2020
Synthesis of difluoromethylated allenes through trifunctionalization of 1,3-enynes.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- N-Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Conglomerate Crystallization in the Cambridge Structural Database (2020-2021).Crystal growth & design · 2023Article
- Radical transformations for allene synthesis.Chemical science · 2022Review
- Radical 1,2,3-tricarbofunctionalization of α-vinyl-β-ketoesters enabled by a carbon shift from an all-carbon quaternary center.Chemical science · 2022Article
- Zinc Iodide Catalyzed Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones.ACS omega · 2021Article
- Direct synthesis of pentasubstituted pyrroles and hexasubstituted pyrrolines from propargyl sulfonylamides and allenamides.Chemical science · 2021Article
- Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling ofEuropean journal of organic chemistry · 2021Article
- Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from spNature communications · 2021Article
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Authors and funding
10 authors.
Funding
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Abstract
Organofluorine compounds have shown their great value in many aspects. Moreover, allenes are also a class of important compounds. Fluorinated or fluoroalkylated allenes might provide an option as candidates for drug and material developments, as allenes allow a great number of valuable transformations. Herein, we report a metal-free synthesis of difluoromethylated allenes via regioselective trifunctionalization of 1,3-enynes. This method proceeds through double C-F bond formation with concomitant introduction of an amino group to the allene. Synthetic applications are conducted and preliminary mechanistic studies suggest that a two-step pathway is involved. DFT calculations revealed an unusual dibenzenesulfonimide-assisted fluorination/fluoroamination with NFSI. In addition, kinetic reaction study revealed the induction period of both major and side products to support the proposed reaction mechanism. This work offers a convenient approach for the synthesis of a range of difluoromethylated allenes and is also a rare example of trifunctionalization of 1,3-enynes.
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