Mechanochemical Solvent‐Free Catalytic C−H Methylation

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...

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Bibliographic Details
Published in:Angewandte Chemie 2021-03, Vol.133 (12), p.6734-6740
Main Authors: Ni, Shengjun, Hribersek, Matic, Baddigam, Swarna K., Ingner, Fredric J. L., Orthaber, Andreas, Gates, Paul J., Pilarski, Lukasz T.
Format: Article
Language:English
Subjects:
arenes
Aromatic compounds
Bioactive compounds
Biological activity
Chemistry
C−H functionalization
mechanochemistry
Methylation
Organometallic complexes
organometallics
Rhodium
Solvents
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Summary: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. Catalytic C−H methylation proceeds efficiently under solvent‐free, mechanochemical conditions, including the late‐stage functionalization of biologically active substrates and otherwise difficult‐to‐make metalacyclic complexes.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202010202