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

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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… Click to show full 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.

Keywords: lewis acid; weiss reagent; phi dmap; acid activation; phi pyr

Journal Title: Chemical communications
Year Published: 2021

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