Recyclable heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes: Practical access to vicinal tricarbonyls

• Published in: Tetrahedron letters 2021-03, Vol.68, p.152953, Article 152953
• Main Authors: Hu, Wenli, Huang, Bin, Niu, Bingbo, Cai, Mingzhong
• Format: Article
• Language: English
• Subjects: 1,2,3-Tricarbonyl; Acylalkyne; Gold; Heterogeneous catalysis; Oxidation
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2021.152953

[Display omitted] •The Ph2P-MCM-41-AuNTf2 complex can be easily prepared by a simple procedure.•Heterogeneous gold-catalyzed oxidation of internal acylalkynes is first reported.•The reaction generates a variety of vicinal tricarbonyls in moderate to high yields.•The Au(I) catalyst can be reused at least 7 times with almost consistent activity.•Our catalytic system provides a novel and practical route to vicinal tricarbonyls. A highly efficient heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes has been developed using 2,6-dichloropyridine N-oxide as the oxidant in dichloromethane (CH2Cl2) at room temperature, providing a novel and practical approach for the construction of diverse vicinal tricarbonyls such as α,β-diketoesters, 1,2,3-triketones, and α,β-diketoamides in good to excellent yields. The heterogeneous gold(I) catalyst can be readily obtained via a simple preparative procedure from commercially available reagents and recovered by filtration of the reaction mixture and reused up to seven times without significant loss of catalytic efficiency.