4.8 Article

α-Arylation of Ketimines with Aryl Sulfides at a Low Palladium Catalyst Loading

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 14, Pages 4573-4576

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600248

Keywords

-arylation; aryl sulfides; C-S bond cleavage; homogeneous catalysis; palladium

Funding

  1. ACT-C, JST
  2. MEXT [25107002]
  3. JSPS [24685007, 26620081]
  4. Grants-in-Aid for Scientific Research [14F04335, 26620081, 25107002, 24685007] Funding Source: KAKEN

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Instead of using aryl halides, aryl sulfides, typically poisonous to transition-metal catalysts, were found to serve as aryl electrophiles in the catalytic -arylation of ketimines, a class of carbonyl derivatives. Low catalyst loadings (down to 0.5mol%) of a palladium-NHC complex are sufficient for efficient arylation. -Arylated ketimine products are useful for the synthesis of various azaarenes, including 2,3-diarylpyrroles, an indole, and pyrrolediones.

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