Denisenko IN, Varzatskii OA, Selin RA, Belov AS, Lebed EG, Vologzhanina AV, Zubavichus YV, Voloshin YZ (2018)
Publication Type: Journal article
Publication year: 2018
Book Volume: 8
Pages Range: 13578-13587
Journal Issue: 24
DOI: 10.1039/c8ra01819g
A new approach for performing Suzuki-Miyaura and Sonogashira reactions of iron(ii) dihalogenoclathrochelates, optimizing their reaction conditions (such as temperature, solvent and a palladium-containing catalyst) and the nature of other reagents (such as arylboron components) is elaborated. These palladium-catalyzed reactions are very sensitive to the nature of the macrobicyclic substrates. The reactivity of the leaving halogen atoms correlates with their ability to undergo an oxidative addition, decreasing in the order: I > Br > Cl, and iron(ii) diiodoclathrochelate underwent these C-C cross-couplings under their "classical" conditions. Phenylboronic, 4-carboxyphenylboronic and 6-ethoxy-2-naphthylboronic acids, and the diethyl ether of 4-(ethoxycarbonyl)boronic acid were tested as components of Suzuki-Miyaura reactions in DMF and in THF. The highest yields of the target products were obtained in DMF, while the highest activation was observed with sodium and potassium carbonates. The Suzuki-Miyaura reaction of a diiodoclathrochelate with 6-ethoxy-2-naphthylboronic acid gave the mono- and difunctionalized clathrochelates resulting from the tandem hydrodeiodination-C-C cross-coupling and double C-C cross-coupling reactions, respectively. Its Sonogashira reactions with trimethylsilylacetylene and acetylenecarboxylic acid in THF and in DMF were tested. This palladium-catalyzed reaction with a (CH
APA:
Denisenko, I.N., Varzatskii, O.A., Selin, R.A., Belov, A.S., Lebed, E.G., Vologzhanina, A.V.,... Voloshin, Y.Z. (2018). Extension and functionalization of an encapsulating macrobicyclic ligand using palladium-catalyzed Suzuki-Miyaura and Sonogashira reactions of iron(ii) dihalogenoclathrochelates with inherent halogen substituents. RSC Advances, 8(24), 13578-13587. https://doi.org/10.1039/c8ra01819g
MLA:
Denisenko, Irina N., et al. "Extension and functionalization of an encapsulating macrobicyclic ligand using palladium-catalyzed Suzuki-Miyaura and Sonogashira reactions of iron(ii) dihalogenoclathrochelates with inherent halogen substituents." RSC Advances 8.24 (2018): 13578-13587.
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