4.8 Article

Azulenesulfonium Salts: Accessible, Stable, and Versatile Reagents for Cross-Coupling

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 7, Pages 2564-2568

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510666

Keywords

azulenes; sulfonium salts; sulfoxides; Suzuki-Miyaura cross-coupling; synthetic methods

Funding

  1. University of Bath
  2. EPSRC [EP/L027267/1]
  3. Engineering and Physical Sciences Research Council [EP/L027267/1] Funding Source: researchfish
  4. EPSRC [EP/L027267/1] Funding Source: UKRI

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Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an SEAr reaction. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling. Specifically, their application in Suzuki-Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.

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