Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides without inert gas protection

[Display omitted] •Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides.•Significant yield promotion by grinding auxiliary addition.•No inert gas protection required. A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which aff...

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Bibliographic Details
Published inTetrahedron letters Vol. 59; no. 23; pp. 2277 - 2280
Main Authors Shao, Qiao-Ling, Jiang, Zhi-Jiang, Su, Wei-Ke
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.2018
Elsevier
Subjects
Aryl chloride
Buchwald-Hartwig amination
Chemistry
Chemistry, Organic
Inert gas protection free
Mechanochemistry
Physical Sciences
Science & Technology
Buchwald-Hartwig amination
Inert gas protection free
Mechanochemistry
Aryl chloride
HALIDES
ACTIVATION
COMPLEXES
SUZUKI-MIYAURA REACTION
SOLID-STATE
PALLADIUM-CATALYZED AMINATION
CROSS-COUPLING REACTIONS
LIGAND
BALL-MILLING CONDITIONS
HECK REACTION
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Summary:[Display omitted] •Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides.•Significant yield promotion by grinding auxiliary addition.•No inert gas protection required. A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which afforded the desired products with moderate to high yields. The addition of sodium sulfate was found to be crucial for improving both the performance and the reproducibility. Comparative solvent-free stirring experiments implicated the importance of mechanical interaction for the transformation, and the inert gas was proved to be unnecessary for this amination.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.04.078