Pfeiffer effect on configurationally labile dyes within ternary complexes with metal ions and enantiopure macrocycles

Pál, Dávid; Lacour, Jérôme

doi:10.1039/d3dt04098d

Dalton Trans.

2024

DOI: 10.1039/d3dt04098d

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Pfeiffer effect on configurationally labile dyes within ternary complexes with metal ions and enantiopure macrocycles

Dávid Pál,

Jérôme Lacour

Abstract: A configurationally-labile helical dye, 2,4,5,7-tetranitrofluorenone oximate, is used to probe complexes made of enantiopure macrocycles and mono/divalent metal ions. Induced electronic circular dichroism (ECD) and 1H NMR responses are amplified...

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

Zhong,

de Aguirre,

Besnard

et al. 2024

Adv Synth Catal

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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 Csp2‐H insertion reactions that derail the targeted reactivity. However, with Pd(acac)2, 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

show abstract

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

Zhong,

de Aguirre,

Besnard

et al. 2024

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

show abstract

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Pfeiffer effect on configurationally labile dyes within ternary complexes with metal ions and enantiopure macrocycles

Abstract: A configurationally-labile helical dye, 2,4,5,7-tetranitrofluorenone oximate, is used to probe complexes made of enantiopure macrocycles and mono/divalent metal ions. Induced electronic circular dichroism (ECD) and 1H NMR responses are amplified...

Cited by 1 publication

References 36 publications

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

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

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