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Research Advances in Organofluorine Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (28 February 2025) | Viewed by 5394

Special Issue Editor


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Guest Editor
Department of Chemistry, Shanghai University, Shanghai 200444, China
Interests: organic chemistry

Special Issue Information

Dear Colleagues,

Organofluorine chemistry stands as a vibrant and pivotal field within the realm of organic synthesis and material science. The incorporation of fluorine atoms into organic molecules brings about a plethora of enhancements in their physical, chemical, and biological properties, leading to applications ranging from pharmaceuticals to advanced materials.

The significance of organofluorine compounds is vividly evident in modern society. Their utilization in drug design, agrochemical development, and materials engineering has propelled scientific innovation. The introduction of fluorine imparts desirable characteristics such as lipophilicity, increased metabolic stability, altered reactivity, and heightened bioactivity to molecules. This has translated into an impressive surge in the percentage of commercial pharmaceuticals and agrochemicals integrating fluorine moieties, with these figures continuously on the rise.

The synthesis of organofluorine compounds, however, is a challenging endeavor due to the scarcity of naturally occurring fluorinated molecules. Consequently, synthetic chemists have fervently explored various strategies to introduce fluorine atoms into organic substrates. Novel methodologies and versatile fluorine-containing reagents have emerged, diversifying the toolkit for creating fluorinated compounds. Moreover, fluorine-containing building blocks have proven invaluable in constructing complex molecules, further catalyzing advances in the field.

This Special Issue on Organofluorine Chemistry is dedicated to unraveling the latest breakthroughs, innovative methodologies, and exciting applications within this domain. Researchers are invited to contribute their work on novel synthetic routes, investigation of unique properties and interactions of organofluorine molecules, and their impact on diverse disciplines. This platform provides an opportunity to deepen our understanding of organofluorine chemistry's dynamic landscape and its continuous role in shaping modern science and technology.

Dr. Jin-Hong Lin
Guest Editor

Manuscript Submission Information

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Keywords

  • fluorine fluorination reactions
  • fluorine incorporation
  • organic fluorine compounds
  • novel fluorine-containing reagents
  • fluorination synthetic strategies
  • fluorine catalysis

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Published Papers (4 papers)

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Research

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9 pages, 1119 KiB  
Article
1,2-Oxidative Trifluoromethylation of Olefin with Ag(O2CCF2SO2F) and O2: Synthesis of α-Trifluoromethyl Ketones
by Shengxue Zhang, Wangchuan Xiao, Jingjing Wu, Fanhong Wu, Houjin Huang, Xiaoyu Ma, Yafei Shi and Chao Liu
Molecules 2024, 29(23), 5622; https://doi.org/10.3390/molecules29235622 - 27 Nov 2024
Viewed by 764
Abstract
A novel and efficient 1,2-oxidative trifluoromethylation of olefins employing Ag(O2CCF2SO2F) as a trifluoromethyl source is described with O2 as the oxidant, which provides access to a variety of valuable α-trifluoromethyl-substituted ketones. The broad substrate scope, feasibility [...] Read more.
A novel and efficient 1,2-oxidative trifluoromethylation of olefins employing Ag(O2CCF2SO2F) as a trifluoromethyl source is described with O2 as the oxidant, which provides access to a variety of valuable α-trifluoromethyl-substituted ketones. The broad substrate scope, feasibility of large-scale operation, and derivatization reactions of α-trifluoromethyl ketones demonstrate the promising utility of this protocol. Full article
(This article belongs to the Special Issue Research Advances in Organofluorine Chemistry)
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16 pages, 3203 KiB  
Article
Photocurable Hypervalent Fluorinated Sulfur Containing Thin Films with Remarkable Hardness and Modulus
by Kelly A. Bonetti, Deniz Rende, Michael Murphy and John T. Welch
Molecules 2024, 29(18), 4413; https://doi.org/10.3390/molecules29184413 - 17 Sep 2024
Viewed by 865
Abstract
Novel tetrafluoro-λ6-sulfanyl-containing oligomers prepared by visible light-promoted addition of 1,4-(bis-chlorotetrafluoro-λ6-sulfanyl) benzene or 1,3-(bis-chlorotetrafluoro-λ6-sulfanyl) benzene to either 1,4-diethynyl benzene or the 1,3-diethynyl isomers form hard, stress resistant thin films on spin casting. The isomeric oligomers were utilized to [...] Read more.
Novel tetrafluoro-λ6-sulfanyl-containing oligomers prepared by visible light-promoted addition of 1,4-(bis-chlorotetrafluoro-λ6-sulfanyl) benzene or 1,3-(bis-chlorotetrafluoro-λ6-sulfanyl) benzene to either 1,4-diethynyl benzene or the 1,3-diethynyl isomers form hard, stress resistant thin films on spin casting. The isomeric oligomers were utilized to establish a structure-function relationship for the mechanical properties of films prepared from the oligomers. The Young’s moduli of 145-nm-thick cured films could reach 60 GPa. The measured hardnesses, between 1.57 and 2.77 GPa, were more than double those of polymethyl methacrylate (PMMA) films. Curing of the tetrafluoro-λ6-sulfanyl-containing polymer films by UV irradiation resulted in coatings that exhibited remarkable hardness and modulus with good surface adhesion to silicon. Full article
(This article belongs to the Special Issue Research Advances in Organofluorine Chemistry)
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10 pages, 1969 KiB  
Article
Efficient Trifluoromethylation of Halogenated Hydrocarbons Using Novel [(bpy)Cu(O2CCF2SO2F)2] Reagent
by Xiong Wu, Xin Qiu, Wenrun Lou, Shengxue Zhang, Chaoyi Zhang, Xiaoyu Ma and Chao Liu
Molecules 2024, 29(12), 2849; https://doi.org/10.3390/molecules29122849 - 14 Jun 2024
Cited by 1 | Viewed by 1180
Abstract
This study introduces a novel trifluoromethylating reagent, [(bpy)Cu(O2CCF2SO2F)2], notable for not only its practical synthesis from cost-effective starting materials and scalability but also its nonhygroscopic nature. The reagent demonstrates high efficiency in facilitating trifluoromethylation reactions [...] Read more.
This study introduces a novel trifluoromethylating reagent, [(bpy)Cu(O2CCF2SO2F)2], notable for not only its practical synthesis from cost-effective starting materials and scalability but also its nonhygroscopic nature. The reagent demonstrates high efficiency in facilitating trifluoromethylation reactions with various halogenated hydrocarbons, yielding products in good yields and exhibiting broad functional group compatibility. The development of [(bpy)Cu(O2CCF2SO2F)2] represents an advancement in the field of organic synthesis, potentially serving as a valuable addition to the arsenal of existing trifluoromethylating agents. Full article
(This article belongs to the Special Issue Research Advances in Organofluorine Chemistry)
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Review

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47 pages, 13335 KiB  
Review
Recent Progress in Synthesis of Alkyl Fluorinated Compounds with Multiple Contiguous Stereogenic Centers
by Xuemei Yin, Xihong Wang, Lei Song, Junxiong Zhang and Xiaoling Wang
Molecules 2024, 29(15), 3677; https://doi.org/10.3390/molecules29153677 - 2 Aug 2024
Cited by 1 | Viewed by 1891
Abstract
Organic fluorides are widely used in pharmaceuticals, agrochemicals, material sciences, and other fields due to the special physical and chemical properties of fluorine atoms. The synthesis of alkyl fluorinated compounds bearing multiple contiguous stereogenic centers is the most challenging research area in synthetic [...] Read more.
Organic fluorides are widely used in pharmaceuticals, agrochemicals, material sciences, and other fields due to the special physical and chemical properties of fluorine atoms. The synthesis of alkyl fluorinated compounds bearing multiple contiguous stereogenic centers is the most challenging research area in synthetic chemistry and has received extensive attention from chemists. This review summarized the important research progress in the field over the past decade, including asymmetric electrophilic fluorination and the asymmetric elaboration of fluorinated substrates (such as allylic alkylation reactions, hydrofunctionalization reactions, Mannich addition reactions, Michael addition reactions, aldol addition reactions, and miscellaneous reactions), with an emphasis on synthetic methodologies, substrate scopes, and reaction mechanisms. Full article
(This article belongs to the Special Issue Research Advances in Organofluorine Chemistry)
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