4.6 Article

DMSO as a Switchable Alkylating Agent in Heteroarene C-H Functionalization

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 40, Pages 10064-10068

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802352

Keywords

C-H functionalization; heteroarenes; methylation; methylthiomethylation; photoredox catalysis

Funding

  1. Alexander von Humboldt Foundation
  2. Deutsche Forschungsgemeinschaft
  3. NRW Graduate School of Chemistry

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Herein, we report a novel strategy for the activation of DMSO to act as a versatile alkylating agent in heteroarene C-H functionalization. This direct, simple, and mild switch between methylation/trideuteromethylation and methylthiomethylation of heteroarenes was achieved under reagent-controlled photoredox catalysis conditions. The proposed mechanism is supported by both experimental and computational studies.

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