Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination.
作者： Young-Ho Oh , Hyoju Choi , Chanho Park , Dong Wook Kim , Sungyul Lee
DOI: 10.3390/MOLECULES25030721
关键词: Combinatorial chemistry 、 Nucleophilic aromatic substitution 、 Nucleophile 、 Ionic bonding 、 Hydrogen bond 、 Chemistry 、 SN2 reaction 、 Solvent 、 Ionic liquid 、 Electrophile
摘要: We review recent works for nucleophilic fluorination of organic compounds in which the Coulombic interactions between ionic species and/or hydrogen bonding affect outcome reaction. SN2 aliphatic promoted by liquids is first discussed, focusing on mechanistic features reaction using alkali metal fluorides. The influence interplay liquid cation, anion, nucleophile and counter-cation treated detail. role as bifunctional (both electrophilic nucleophilic) activator envisaged. also SNAr diaryliodonium salts from same perspective. Nucleophilic guanidine-containing salts, are capable forming bonds with nucleophile, exemplified an excellent case where significantly efficiency origin experimental observation strong dependence yields positions -Boc protection understood terms location respect to center, being either close far it. Recent advances synthesis [18F]F-dopa cited relation salts. Discussions made a focus tailor-making promoters solvent engineering based bonding.
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