Scientific article

Pd‐Catalyzed [3+6+3+6] Macrocyclizations of Aryl α‐Diazo‐β‐Ketoesters

Published inAdvanced synthesis & catalysis, adsc.202400118
Publication date2024-05-06
First online date2024-05-06

Thanks to Pd(II)‐catalysis, an efficient synthesis of unsaturated macrocycles is achieved by [3+6+3+6] condensation of cyclic ethers with aryl α‐diazo‐β‐ketoesters. The presence of the electron‐rich aryl ester moieties forbids the use of dirhodium complexes as these diazo decomposition catalysts provoke unforeseen intermolecular C<sub>sp2</sub>‐H insertion reactions that derail the targeted reactivity. However, with Pd(acac)<sub>2</sub>, using high concentration conditions (1 M), a variety of 18‐membered macrocycles (16 examples) is 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

Citation (ISO format)
ZHONG, Zhuang et al. Pd‐Catalyzed [3+6+3+6] Macrocyclizations of Aryl α‐Diazo‐β‐Ketoesters. In: Advanced synthesis & catalysis, 2024, p. adsc.202400118. doi: 10.1002/adsc.202400118
Main files (1)
Article (Accepted version)
accessLevelRestrictedaccessLevelPublic 05/07/2025
ISSN of the journal1615-4150

Technical informations

Creation05/29/2024 8:20:06 AM
First validation05/29/2024 12:49:17 PM
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