Issue 91, 2021

Lewis acid activation of Weiss’ reagents ([PhI(Pyr)2]2+) with boranes and isolation of [PhI(4-DMAP)]2+

Abstract

Abstraction of a pyridine ligand from Weiss’ reagent ([PhI(Pyr)2]2+) using BF3-Et2O was found to activate Weiss’ reagent towards electrophilic aromatic substitution reactions. The activated species can be isolated when 4-DMAP is used as the pyridine ligand and was determined to be [PhI(4-DMAP)]2+ in solution. The isolated cation was reactive in electrophilic aromatic substitution reactions towards mesitylene, xylene and toluene that Weiss’ reagent itself does not react with.

Graphical abstract: Lewis acid activation of Weiss’ reagents ([PhI(Pyr)2]2+) with boranes and isolation of [PhI(4-DMAP)]2+

Supplementary files

Article information

Article type
Communication
Submitted
25 8 2021
Accepted
22 10 2021
First published
22 10 2021

Chem. Commun., 2021,57, 12163-12166

Lewis acid activation of Weiss’ reagents ([PhI(Pyr)2]2+) with boranes and isolation of [PhI(4-DMAP)]2+

A. Bakro, L. Sharp-Bucknall, T. B. Poynder, J. K. Clegg, D. J. D. Wilson and J. L. Dutton, Chem. Commun., 2021, 57, 12163 DOI: 10.1039/D1CC04725F

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