4.8 Article

Palladium-Catalyzed Acylation/Alkenylation of Aryl Iodide: A Domino Approach Based on the Catellani-Lautens Reaction

Journal

ACS CATALYSIS
Volume 5, Issue 8, Pages 4927-4931

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b00516

Keywords

palladium; Catellani-Lautens reaction; acylation; alkenylation; carboxylic anhydrides

Funding

  1. National Science Foundation [NSF 21272101, NSF 21472074, NSF 21472073]
  2. MOE
  3. PCSIRT [IRT1138]

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A new palladium-catalyzed three-component coupling involving acylation/alkenylation of aryl iodide is reported. The reaction was carried out with readily available starting materials and gave the ortho-acylated styrene in moderate to good yields. Compared with previous Catellani-Lautens reactions, this reaction is the first example of introducing an acyl group at the ortho position of aryl iodides. The proposed Pd-IV complex, generated via oxidative addition of the carboxylic anhydrides, is a key intermediate for this transformation.

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