Mechanism of electrophilic fluorination with Pd(iv): Fluoride capture and subsequent oxidative fluoride transfer
Electrophilic fluorinating reagents derived from fluoride are desirable for the synthesis of 18F-labeled molecules for positron emission tomography (PET). Here, we study the mechanism by which a Pd(iv)-complex captures fluoride and subsequently transfers it to nucleophiles. The intermediate Pd(iv)-F is formed with high rates even at the nano- to micromolar fluoride concentrations typical for radiosyntheses with 18F due to fast formation of an outer-sphere complex between fluoride and Pd(iv). The subsequent fluorine transfer from the Pd(iv)-F complex is proposed to proceed through an unusual SET/fluoride transfer/SET mechanism. The findings detailed in this manuscript provide a theoretical foundation suitable for addressing a more general approach for electrophilic fluorination with high specific activity 18F PET imaging.
Solvent-free fluorination of organic compounds using N-F reagents
Efficient fluorination of 1,3-dicarbonyl compounds, enol acetates of aromatic ketones, and activated aromatic compounds was achieved under solvent-free conditions using Selectfluor F-TEDA-BF4 or Accufluor NFSi.
Stavber, Gaj,Zupan, Marko,Stavber, Stojan
p. 2671 - 2673
(2008/02/03)
Fluorination with Cesium Fluoroxysulfate. Room-Temperature Fluorination of Benzene and Naphthalene Derivatives
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Stavber, Stojan,Zupan, Marko
p. 3609 - 3612
(2007/10/02)
Caesium Fluoroxysulphate as a Mild Fluorinating Agent for the Fluorination of Alkoxy-substituted Benzene and Naphthalene Derivatives
Room-temperature fluorination of alkoxy-substituted benzene derivatives with caesium fluoroxysulphate in the presence of boron trifluoride as catalyst resulted in the formation of ortho- and para-fluoro-substituted products, the ratio being dependent on the size of the alkoxy-group, while reactions with 2-alkoxynaphthalene derivatives resulted in the formation of 1,1-difluoro-2-oxo-1,2-dihydronaphthalene as well as 1-fluoro-substituted products.
Stavber, Stojan,Zupan, Marko
p. 148
(2007/10/02)
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