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Silyldefluorination of Fluoroarenes by Concerted Nucleophilic Aromatic Substitution
Author(s) -
Mallick Shubhadip,
Xu Pan,
Würthwein ErnstUlrich,
Studer Armido
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808646
Subject(s) - chemistry , nucleophilic substitution , aryl , silylation , nucleophile , nucleophilic aromatic substitution , reagent , substitution reaction , lithium (medication) , silanes , electrophilic aromatic substitution , medicinal chemistry , photochemistry , organic chemistry , alkyl , catalysis , medicine , silane , endocrinology
Abstract The reaction of readily generated silyl lithium reagents with various aryl fluorides to provide the corresponding aryl silanes is reported. DFT calculations reveal that the nucleophilic aromatic substitution of the fluoride anion by the silyl lithium reagent proceeds through concerted ipso substitution. In contrast to the classical nucleophilic aromatic substitution, this concerted ionic silyldefluorination also occurs on more electron‐rich aryl fluorides.