Journalartikel

Autorenliste: de Meijere, A; Stulgies, B; Albrecht, K; Rauch, K; Wegner, HA; Hopf, H; Scott, LT; Eshdat, L; Aprahamian, I; Rabinovitz, M

Jahr der Veröffentlichung: 2006

Seiten: 813-830

Zeitschrift: Pure and Applied Chemistry: The Scientific Journal of IUPAC

Bandnummer: 78

Heftnummer: 4

ISSN: 0033-4545

DOI Link: https://doi.org/10.1351/pac200678040813

Verlag: De Gruyter

Abstract: 
Modern transition-metal-catalyzed cross-coupling reactions, especially of the Kumada, Heck, and Suzuki types, have provided facile access to various bridge-annelated [2.2]paracyclophane derivatives including trifoliaphane and its tribenzo analog. The reduction of trifoliaphane with potassium metal in [D-8]-THF led to hexakis[p-benzyl]benzene anion, which could efficiently be trapped with various electrophiles. Highly efficient multifold Suzuki couplings were performed with hexabromobenzene, octabromonaphthalene, and hexabromotriphenylene. The obtained hexa- and octaalkenylarene derivatives disclose interesting molecular shapes. Eventually, a newly developed cascade Coupling of bromoarenes containing peri-positioned C-H bonds has led to indeno-annelated polycyclic aromatic hydrocarbons including indenocorannulene as well as the tetrakis- and tris(tert-butyl-indeno)pyrene which disclose very interesting spectroscopic properties. In particular, tetrakis(tert-butylindeno)pyrene self-assembles in solution by way of pi-stacking, and it can be reduced with potassium metal to a stable dianion, a readily dimerizing trianion radical, and a tetraanion.

Harvard-Zitierstil: de Meijere, A., Stulgies, B., Albrecht, K., Rauch, K., Wegner, H., Hopf, H., et al. (2006) New interesting molecular topologies by way of modern cross-coupling reactions, Pure and Applied Chemistry, 78(4), pp. 813-830. https://doi.org/10.1351/pac200678040813

APA-Zitierstil: de Meijere, A., Stulgies, B., Albrecht, K., Rauch, K., Wegner, H., Hopf, H., Scott, L., Eshdat, L., Aprahamian, I., & Rabinovitz, M. (2006). New interesting molecular topologies by way of modern cross-coupling reactions. Pure and Applied Chemistry. 78(4), 813-830. https://doi.org/10.1351/pac200678040813