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.
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.
The reaction of unactivated secondary
and primary alkyl chlorides
as well as primary alkyl triflates with silyl lithium reagents to
access tetraorganosilanes is reported. These nucleophilic substitutions
proceed in the absence of any transition metal catalyst under mild
conditions in moderate to very good yields. The silyl lithium reagents
are readily generated from the corresponding commercially available
chlorosilanes. Enantioenriched secondary alkyl chlorides react with
high stereospecificity under inversion of configuration.
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