Nanocellulose as Reaction Medium for FeCl3-Mediated Mechanochemical Deaminative Fluorination of (Hetero)aromatic AminesShow others and affiliations
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
2025-07-082025-07-082025-07-08Bibliographically approved