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Scientific article
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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
Abstract

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

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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
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Article (Accepted version)
accessLevelRestrictedaccessLevelPublic 05/07/2025
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ISSN of the journal1615-4150
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