Organofluorine compounds have revolutionized chemical and pharmaceutical industries, serving as essential components in numerous applications and aspects of modern life. However, their bioaccumulation and resistance to degradation have resulted in environmental pollution, posing significant risks to human and animal health. The exceptionally strong C-F bond in these compounds makes their degradation challenging, with current methods often requiring extreme experimental conditions. Therefore, the development of eco-friendly approaches that operate under milder conditions is crucial, with enzyme-mediated C-F bond cleavage strategies emerging as a particularly promising solution. In this review, we present an overview of how computational approaches, including molecular docking, molecular dynamics simulations, quantum mechanics/molecular mechanics calculations, and bioinformatics, have been utilized to investigate the mechanisms underlying enzymatic C-F bond degradation and functionalization. This review highlights how these computational approaches provide critical insights into the atomic-level interactions and energetics underlying enzymatic processes, offering a foundation for the rational design and engineering of enzymes capable of addressing the challenges posed by fluorinated compounds. This review covers several types of enzymes including: fluoroacetate dehalogenases, cysteine dioxygenase, L-2-haloacid dehalogenase, cytochrome P450, fluorinase and tyrosine hydroxylase.
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http://dx.doi.org/10.1002/cphc.202401130 | DOI Listing |
Environ Sci Technol
March 2025
School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
Halogenated antibiotics pose a great threat to aqueous environments because of their persistent biotoxicity from carbon-halogen bonds. Electrochemical reduction (ER) is an efficient technology for dehalogenation, but it still suffers from limited efficiencies in breaking C-F bonds. Herein, we present a strategy to enhance C-F cleavage and promote detoxification by loading benchmark palladium cathodes onto boron-doped carbon.
View Article and Find Full Text PDFChem Sci
February 2025
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University 222 South Tianshui Road Lanzhou 730000 People's Republic of China
A transition-metal-free protocol for the unsymmetrical radical 1,3-difunctionalization of alkenes has been established for the first time in the form of 1,3-difluoroalkylcarboxylation by a photocatalytic radical three-component reaction of allyl formates, trifluoroacetanilides, and cesium formate. This reaction employs formate as the carboxylating reagent and trifluoroacetanilide as the difluoroalkylating reagent C-F bond activation. As a result, a series of previously inaccessible unsymmetrical difluorinated adipic acid derivatives can be easily and efficient prepared.
View Article and Find Full Text PDFOrg Lett
March 2025
Key Laboratory of Molecular and Nano Probes, Ministry of Education, College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, China.
A controlled cleavage of double C-F bonds in sterically hindered tetrasubstituted CF-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized -difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination and C-F bond carboxylation with good-to-high yields. Precisely controlling the quantity of formate salt and the reaction time is crucial for obtaining divergent defluorinative products.
View Article and Find Full Text PDFJ Am Chem Soc
March 2025
Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, Lausanne CH-1015, Switzerland.
Under the Pd(II)/Pd(IV) catalytic cycle, the cyclization of pent-4-en-1-amine derivatives typically yields either pyrrolidines or piperidines depending on the N-protecting group. We report herein an unprecedented Pd(II)-catalyzed oxidative domino process that converts readily accessible N-protected 2-(2-amidoethyl)-1-methylenecyclobutane derivatives to 1-fluoro-2-azabicyclo[3.2.
View Article and Find Full Text PDFJACS Au
February 2025
Department of Chemistry, Gwangju Institute of Science and Technology, Gwangju 61005, Republic of Korea.
Through the prosperity of organofluorine chemistry in modern organic synthesis, perfluorinated organic compounds are now abundant and widely available. Consequently, these substances become attractive starting materials for the production of complex, multifunctional fluorinated molecules. However, the inherent challenges associated with the activation and discrimination of the C-F bonds typically lead to overdefluorination as well as functional group incompatibility.
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