Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination

Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination

We review recent works for nucleophilic fluorination of organic compounds in which the Coulombic interactions between ionic species and/or hydrogen bonding affect the outcome of the reaction. S<sub>N</sub>2 fluorination of aliphatic compounds promoted by ionic liquids is first discussed,...

Full description

Bibliographic Details
Main Authors:	Young-Ho Oh, Hyoju Choi, Chanho Park, Dong Wook Kim, Sungyul Lee
Format:	Article
Language:	English
Published:	MDPI AG 2020-02-01
Series:	Molecules
Subjects:	ionic interactions hydrogen bonding nucleophilic fluorination
Online Access:	https://www.mdpi.com/1420-3049/25/3/721

Similar Items

Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene
by: Javier Ajenjo, et al.
Published: (2016-02-01)

Tunable Synthesis of Predominant Semi-Ionic and Covalent Fluorine Bonding States on a Graphene Surface
by: Jae-Won Lee, et al.
Published: (2021-04-01)

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
by: Marcin Kaźmierczak, et al.
Published: (2020-04-01)

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations
by: Sandeep Kumar Mishra, et al.
Published: (2017-03-01)

Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate
by: Kevin Grollier, et al.
Published: (2020-12-01)

Decomposition of Fluorinated Ionic Liquids to Fluoride Ions Using Superheated Water: An Efficient Approach for Recovering Fluorine from the Waste of Fluorinated Ionic Liquids
by: Hisao HORI
Published: (2021-03-01)

Rh-catalyzed reductive coupling under hydrogenation conditions and nucleophilic catalysis via phosphine conjugate addition
by: Kong, Jongrock, 1972-
Published: (2008)

Studies Toward Highly Fluorinated Polyphenylenes by Diels-Alder Polymerization
by: Sen, Sanghamitra
Published: (2014)

An ab initio Study of the Structure and Energetics of Hydrogen Bonding in Ionic Liquids
by: Kaycee Low, et al.
Published: (2019-04-01)

Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen
by: Jakub Wantulok, et al.
Published: (2021-03-01)

High Solid Fluorescence of a Pyrazoline Derivative through Hydrogen Bonding
by: Liang Zhang, et al.
Published: (2017-08-01)

<sup>18</sup>F-Fluorination Using Tri-<i>Tert</i>-Butanol Ammonium Iodide as Phase-Transfer Catalyst: An Alternative Minimalist Approach
by: Sandip S. Shinde, et al.
Published: (2021-08-01)

MÉTODOS SELETIVOS DE FLUORAÇÃO DE MOLÉCULAS ORGÂNICAS
by: Núbia Boechat, et al.
Published: (2015-12-01)

Unimolecular Solvolyses in Ionic Liquid: Alcohol Dual Solvent Systems
by: Elizabeth D. Kochly, et al.
Published: (2016-01-01)

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles
by: Anton Yu. Shabalin, et al.
Published: (2017-04-01)

The First Example of Oxidative Nucleophilic Substitution of Hydrogen in meso-Aryl Ring of the 5,10,15,20-Tetraphenylporphyrin Derivatives
by: Agnieszka Mikus, et al.
Published: (2006-12-01)

C(aryl)-O Bond Formation from Aryl Methanesulfonates via Consecutive Deprotection and SNAr Reactions with Aryl Halides in an Ionic Liquid
by: Hui Xu, et al.
Published: (2007-04-01)

The Topological Analysis of the ELF<sub>x</sub> Localization Function: Quantitative Prediction of Hydrogen Bonds in the Guanine–Cytosine Pair
by: Johanna Klein, et al.
Published: (2021-06-01)

Fluorinated Alcohols : A Perfect Medium for Direct Functionalization of Aromatics
by: Tang, Renjin
Published: (2018)

Nucleophilicities of Lewis Bases B and Electrophilicities of Lewis Acids A Determined from the Dissociation Energies of Complexes B⋯A Involving Hydrogen Bonds, Tetrel Bonds, Pnictogen Bonds, Chalcogen Bonds and Halogen Bonds
by: Ibon Alkorta, et al.
Published: (2017-10-01)

Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles
by: Ziyi Li, et al.
Published: (2020-10-01)

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides
by: Masanori Inaba, et al.
Published: (2018-01-01)

Intramolecular C-H···O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives
by: Brigita Cekavicus, et al.
Published: (2011-09-01)

Tailor-Made Fluorinated Ionic Liquids for Protein Delivery
by: N. S. M. Vieira, et al.
Published: (2020-08-01)

Designing Acrylic Block Copolymers with Multiple Hydrogen Bonding or Multiple Ionic Bonding
by: Chen, Xi
Published: (2018)

Flexibility of Hydrogen Bond and Lowering of Symmetry in Proton Conductor
by: Seiichiro Ikehata, et al.
Published: (2012-08-01)

Fluorinated azobenzenes as supramolecular halogen-bonding building blocks
by: Esther Nieland, et al.
Published: (2019-08-01)

Bond orders for intermolecular interactions in crystals: charge transfer, ionicity and the effect on intramolecular bonds
by: Khidhir Alhameedi, et al.
Published: (2018-09-01)

Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine
by: Jianlin Han, et al.
Published: (2020-04-01)

Infinite dilution activity coefficient measurements of organic solutes in fluorinated ionic liquids by gas-liquid chromatography and the inert gas stripping method
by: Tumba, Armel Kaniki.
Published: (2010)

Ionic strength and hydrogen bonding effects on whey protein isolate–flaxseed gum coacervate rheology
by: Jun Liu, et al.
Published: (2020-04-01)

Bridging Mesoscale Phenomena and Macroscopic Properties in Block Copolymers Containing Ionic Interactions and Hydrogen Bonding
by: Chen, Mingtao
Published: (2018)

Mechanistic Investigation of Metal Promoted Nucleophilic Additions
by: Arun Kumar, P
Published: (2017)

New Nucleophilic Organocatalysts
by: Harris, David T.
Published: (2011)

Sulfur - fluorine bond in PET radiochemistry
by: Giancarlo Pascali, et al.
Published: (2017-07-01)

Reversible nucleophilic addition : a new approach to asymmetric catalysis
by: Sohal, Gian Singh
Published: (2001)

A theoretical study of the global and local electrophilicity, nucleophilicity, polarizability and QTAIM theory for calix[4]arene-gas interaction
by: B. Gassoumi, et al.
Published: (2020-07-01)

Regioselective, Nucleophilic Activation of C-F Bonds in o-Fluoroanilines
by: Hough, Sarita Elizabeth
Published: (2019)

New methods for nucleophilic fluorination
by: Cresswell, Alex
Published: (2011)

Exploring Multiple Hydrogen Bonding and Ionic Bonding in the Design of Supramolecular Polymers
by: Chen, Xi
Published: (2020)