Dataset for Pd-Catalyzed [3+6+3+6] Macrocyclizations of Aryl alpha-Diazo-beta-Ketoesters

Thanks to Pd(II)-catalysis, an efficient synthesis of unsaturated macrocycles is achieved by [3+6+3+6] condensation of cyclic ethers with aryl alpha-diazo-beta-ketoesters. The presence of the electron-rich aryl ester moieties forbids the use of dirhodium complexes as these diazo decomposition catalysts provoke unforeseen intermolecular Csp2-H insertion reactions that derail the targeted reactivity. With Pd(acac)2, using high concentration conditions (1 M), a variety of 18-membered macrocycles (16 examples) is however afforded with both aryl and alkyl diazo reagents. Catalyst selection for either electrophilic aromatic substitution (Rh) or ylide (Pd) pathways are explained by computational approaches.

    Organizational unit
    Laboratory of Professor Jérôme Lacour
    Type
    Dataset
    DOI
    10.26037/yareta:gjrfvaftzfggxmvlwf5l6dzkhy
    License
    Creative Commons Attribution 4.0 International
Publication date31/01/2024
Retention date28/01/2034
accessLevelPublicAccess levelPublic
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Contributors
  • Zhong, Zhuang
  • de Aguirre, Adiran
  • Besnard, Céline orcid
  • Poblador Bahamonde, Amalia orcid
  • Lacour, Jérôme orcid
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