Copper-Mediated C–N Coupling of Arylsilanes with Nitrogen Nucleophiles

A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor ar...

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Bibliographic Details
Published in:Organic letters 2016-10, Vol.18 (20), p.5244-5247
Main Authors: Morstein, Johannes, Kalkman, Eric D, Cheng, Chen, Hartwig, John F
Format: Article
Language:English
Subjects:
amination
aromatic hydrocarbons
carbon-hydrogen bond activation
chemical structure
fluorides
Lewis bases
nitrogen
silylation
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Summary:A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C–H silylation generates arylamines from unactivated arenes with site selectivity controlled by steric effects. This combination of steps gives direct access to many compounds that cannot be accessed via alternative C–H functionalization methods, including direct C–H amination or the combination of C–H borylation and amination.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b02543