4.8 Article

Mechanochemical Solvent-Free Catalytic C-H Methylation

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 12, Pages 6660-6666

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010202

Keywords

arenes; C− H functionalization; mechanochemistry; organometallics; rhodium

Funding

  1. Carl Tryggers Stiftelsen
  2. Swedish Research Council (Vetenskapsradet)

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This new mechanochemical method enables highly regioselective C-H methylation of (hetero)arenes, showing excellent functional-group compatibility and shorter reaction times, and can be used for the synthesis of biologically active compounds.
The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C-H methylation of (hetero)arenes is reported. The reaction shows excellent functional-group compatibility and is demonstrated to work for the late-stage C-H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C-H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.

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