Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension

Linke J, Neumann B, Stammler H-G, Kuck D (2018)
CHEMISTRY-A EUROPEAN JOURNAL 24(37): 9316-9324.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Centrohexaindane was converted into its T-d-symmetrical 2,3,6,7,10,11,14,15,20,21,26,27-dodecabromo and -dodecaiodo derivatives using N-bromo- and N-iodosuccinimide, respectively, in the presence of trifluoromethanesulfonic acid as a catalyst in single, highly efficient steps. Sonication or microwave irradiation was indispensable to enforce exhaustive halogenation of the twelve equivalent peripheral positions of this Cartesian polyaromatic hydrocarbon. Despite their extremely poor solubility in most organic solvents, the new dodecahalo derivatives were fully characterized, including single crystal X-ray structure analysis. Subsequent Pd-0-catalyzed twelve-fold C-C cross-coupling reactions furnished the corresponding dodecamethyl, dodeca(phenylethynyl) and dodecaphenyl derivatives in good to excellent yields. The latter hydrocarbon was also analyzed by X-ray diffraction.
Stichworte
cross coupling; halogenation; multiple functionalization; polycyclic; aromatic compounds; topology
Erscheinungsjahr
2018
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
24
Ausgabe
37
Seite(n)
9316-9324
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2930267

Zitieren

Linke J, Neumann B, Stammler H-G, Kuck D. Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(37):9316-9324.
Linke, J., Neumann, B., Stammler, H. - G., & Kuck, D. (2018). Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension. CHEMISTRY-A EUROPEAN JOURNAL, 24(37), 9316-9324. doi:10.1002/chem.201801806
Linke, J., Neumann, B., Stammler, H. - G., and Kuck, D. (2018). Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension. CHEMISTRY-A EUROPEAN JOURNAL 24, 9316-9324.
Linke, J., et al., 2018. Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension. CHEMISTRY-A EUROPEAN JOURNAL, 24(37), p 9316-9324.
J. Linke, et al., “Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 24, 2018, pp. 9316-9324.
Linke, J., Neumann, B., Stammler, H.-G., Kuck, D.: Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension. CHEMISTRY-A EUROPEAN JOURNAL. 24, 9316-9324 (2018).
Linke, Jens, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “Dodecabromo- and Dodecaiodocentrohexaindane: T-d-Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension”. CHEMISTRY-A EUROPEAN JOURNAL 24.37 (2018): 9316-9324.

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