Substitution of fluorine in M[C6F5BF3] with organolithium compounds: Distinctions between O- and N-nucleophiles

Anton Yu Shabalin, Nicolay Yu Adonin, Vadim V. Bardin

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6F4BF3]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the para position to boron is the predominant route. When R = Ph, the ratio M[4-RC6F4BF3]/M[2-RC6F4BF3] is ca. 1: 1. Substitution of the fluorine atom at the ortho position to boron is solely caused by the coordination of RLi via the lithium atom with the fluorine atoms of the BF3 group. This differs from the previously reported substitution in K[C6F5BF3] by O- and N-nucleophiles that did not produce K[2-NuC6F4BF3].

Original languageEnglish
Pages (from-to)703-713
Number of pages11
JournalBeilstein Journal of Organic Chemistry
Volume13
DOIs
Publication statusPublished - 12 Apr 2017

Keywords

  • C-nucleophile
  • NMR spectroscopy
  • Nucleophilic substitution
  • Pentafluorophenyltrifluoroborate

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