A New Class of SN2 Reactions Catalyzed by Protic Solvents:  Facile Fluorination for Isotopic Labeling of Diagnostic Molecules

DW Kim, DS Ahn, YH Oh, S Lee, HS Kil… - Journal of the …, 2006 - ACS Publications
Aprotic solvents are usually preferred for the SN2 reactions, because nucleophilicity and
hence SN2 reactivity are severely retarded by the influence of the partial positive charge of …

Facile Nucleophilic Fluorination Reactions Using tert-Alcohols as a Reaction Medium:  Significantly Enhanced Reactivity of Alkali Metal Fluorides and Improved …

DW Kim, Jeong, ST Lim, MH Sohn… - The Journal of …, 2008 - ACS Publications
Although protic solvents are generally not preferred for nucleophilic displacement reactions
because of their partial positive charge and hydrogen-bonding capacity that solvate the …

Hydrogen-bond promoted nucleophilic fluorination: concept, mechanism and applications in positron emission tomography

JW Lee, MT Oliveira, HB Jang, S Lee, DY Chi… - Chemical Society …, 2016 - pubs.rsc.org
Due to the tremendous interest in carbon–fluorine bond-forming reactions, research efforts
in this area have been dedicated to the development of facile processes to synthesize small …

Direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO (NTs) CH 2 F: the accelerating effect of α-fluorine substitution

X Shen, M Zhou, C Ni, W Zhang, J Hu - Chemical Science, 2014 - pubs.rsc.org
An efficient and direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO
(NTs) CH2F 1 has been developed. In contrast to the previously known detrimental effect of …

Strategies for Nucleophilic C(sp3)–(Radio)Fluorination

INM Leibler, SS Gandhi, MA Tekle-Smith… - Journal of the …, 2023 - ACS Publications
This Perspective surveys the progress and current limitations of nucleophilic fluorination
methodologies. Despite the long and rich history of C (sp3)–F bond construction in chemical …

Synthesis and reactivity of [18F]-N-fluorobenzenesulfonimide

H Teare, EG Robins, E Årstad, SK Luthra… - Chemical …, 2007 - pubs.rsc.org
A novel [18F] NF reagent and two novel radiochemical transformations have been
developed:[18F] NFSi has been prepared from sodium dibenzenesulfonimide and reacted in …

Stereospecific synthesis of 1-fluoro olefins via (fluorovinyl) stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry

JR McCarthy, EW Huber, TB Le, FM Laskovics… - Tetrahedron, 1996 - Elsevier
(E)-and (Z)-Fluorovinyl sulfones (II) form (fluorovinyl) stannanes (III) on treatment with two
equivalents of tributyltin hydride and a catalytic amount of AIBN; the free radical catalyzed …

Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF

KJ Makaravage, AF Brooks, AV Mossine… - Organic …, 2016 - ACS Publications
A copper-mediated nucleophilic radiofluorination of aryl-and vinylstannanes with [18F] KF is
described. This method is fast, uses commercially available reagents, and is compatible with …

Multiple Approaches to the In Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions

MA Cismesia, SJ Ryan, DC Bland… - The Journal of Organic …, 2017 - ACS Publications
This article focuses on the development of practical approaches to the in situ generation of
anhydrous fluoride salts for applications in nucleophilic aromatic substitution (SNAr) …

[PDF][PDF] Tetrabutylammonium tetra (tert-butyl alcohol)-coordinated fluoride as a facile fluoride source

DW Kim, HJ Jeong, ST Lim, MH Sohn - Angew. Chemie, 2008 - academia.edu
The generally favorable pharmaceutical properties of many low fluorinated compounds and
18F-labeled radiopharmaceuticals for positron emission tomography (PET) molecular …