4.8 Article

Palladium(II)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon-sulfur and carbon-hydrogen bonds

Journal

CHEMICAL SCIENCE
Volume 7, Issue 4, Pages 2587-2591

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04890g

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Funding

  1. MEXT, Japan
  2. JST, Japan

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A new process has been developed for the palladium(II)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C-H and C-S bonds. In contrast to the existing methods for the synthesis of this scaffold by C-H functionalization, this new catalytic C-H/C-S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C-X or S-H, allowing its application to the synthesis of elaborate pi-systems. Notably, the product-forming step of this reaction lies in an oxidative addition step rather than a reductive elimination step, making this reaction mechanistically uncommon.

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