4.8 Article

N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aromatic Aldehydes with Activated Alkyl Halides

Journal

ORGANIC LETTERS
Volume 13, Issue 1, Pages 98-101

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102626p

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Funding

  1. Fonds der Chemischen Industrie
  2. Deutsche Forschungsgemeinschaft (DFG)
  3. International NRW Graduate School of Chemistry
  4. Alexander von Humboldt Foundation
  5. Alfried Krupp von Bohlen and Halbach Foundation

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N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, a-halo ketones and esters can also be used, as aldehyde reaction partners.

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