4.5 Article

Palladium-Catalyzed Amination of Aryl Sulfides with Aliphatic Amines

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 12, Pages 2678-2682

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500226

Keywords

Synthetic methods; Homogeneous catalysis; Amination; Arylation; Sulfur; Carbene ligands; Palladium

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) [25107002]
  2. Japan Society for the Promotion of Science JSPS [24685007, 26620081]
  3. JSPS
  4. Grants-in-Aid for Scientific Research [26620081, 14F04335, 24685007, 25107002] Funding Source: KAKEN

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Conditions for the palladium-NHC-catalyzed amination of aryl sulfides with aliphatic as well as aromatic amines were established. The KHMDS-mediated amination of heteroaryl sulfides could proceed without palladium. Based on the distinct difference in reactivity of C-Br and C-S bonds, a sequential amination of bromothioanisole can take place to install two different alkylamino groups onto the aromatic ring in one pot.

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