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Nanocellulose as Reaction Medium for FeCl3-Mediated Mechanochemical Deaminative Fluorination of (Hetero)aromatic Amines
Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovského 40, 97401, Banska Bystrica, Slovakia.
Department of Heteroatom Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans'ka, 02660, Kyiv, Ukraine.
Department of Chemical Sciences, P. D. Patel Institute of Applied Sciences, Charotar University of Science and Technology (CHARUSAT), Changa 388 421, Gujarat, India.
Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovského 40, 97401, Banska Bystrica, Slovakia.
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2024 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 366, no 15, p. 3269-3276Article in journal (Refereed) Published
Abstract [en]

The development of an efficient alternative to the widely employed Balz-Schiemann deaminative fluorination method (i. e. without using aryl diazonium tetrafluoroborate salt) is a challenging task. Herein, we report a convenient one-pot method for the FeCl3-nanocellullose mediated mechanochemical synthesis of fluoroarenes through the selective substitution of an aromatic amino group by fluorine group using pyrylium tetrafluoroborate (Pyry-BF4) and sodium fluoride (NaF) via in situ formation of pyridinium salt intermediate. The scope of the present protocol includes synthesis of thirty-four organofluorine compounds with excellent yields via a selective substitution (SNAr) of an amino group by fluorine. The presented concise methodology opens a pathway to access new chemical spaces for the late-stage functionalization in pharmaceutical industries.

Place, publisher, year, edition, pages
Wiley , 2024. Vol. 366, no 15, p. 3269-3276
Keywords [en]
deamination, fluorination, Mechanochemistry, nanocellulose, solvent-free, sustainability
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-366662DOI: 10.1002/adsc.202400303ISI: 001271735400001Scopus ID: 2-s2.0-85198746115OAI: oai:DiVA.org:kth-366662DiVA, id: diva2:1982767
Note

QC 20250708

Available from: 2025-07-08 Created: 2025-07-08 Last updated: 2025-07-08Bibliographically approved

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Iaroshenko, Viktor O.

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