Highly regioselective 4-hydroxy-1-methylpiperidine mediated aromatic nucleophilic substitution on a perfluorinated phthalimide core

Ramóna Madácsi, Márió Gyuris, J. Wölfling, L. Puskás, Iván Kanizsai

Research output: Contribution to journalArticle

Abstract

A tertiary amine-mediated highly regioselective aromatic nucleophilic substitution (SNAr) protocol was developed in the assemblies of perfluorinated phtalimide with primary or secondary amines as inputs. Application of 1-methyl-4-hydroxypiperidine as additive, formation of the less favoured, bioactive regioisomer was facilitated, modifying their ratios from the initial 8–36% to 81–91%. After optimization, a facile gram scale syntheses were accomplished and isolated the desired analogues in up to 63% yield.

Original languageEnglish
Pages (from-to)38-44
Number of pages7
JournalJournal of Fluorine Chemistry
Volume212
DOIs
Publication statusPublished - Aug 1 2018

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Keywords

  • Aromatic nucleophilic substitution
  • Phtalimide
  • Regioselective
  • SAr
  • Tertiary amine

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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