Nanocellulose as Reaction Medium for FeCl3-Mediated Mechanochemical Deaminative Fluorination of (Hetero)aromatic AminesVisa övriga samt affilieringar
2024 (Engelska)Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 366, nr 15, s. 3269-3276Artikel i tidskrift (Refereegranskat) 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.
Ort, förlag, år, upplaga, sidor
Wiley , 2024. Vol. 366, nr 15, s. 3269-3276
Nyckelord [en]
deamination, fluorination, Mechanochemistry, nanocellulose, solvent-free, sustainability
Nationell ämneskategori
Organisk kemi
Identifikatorer
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
Anmärkning
QC 20250708
2025-07-082025-07-082025-07-08Bibliografiskt granskad