CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2006, Vol. 78, No. 4, pp. 813-830

New interesting molecular topologies by way of modern cross-coupling reactions

Armin de Meijere1, Baldur Stulgies1, Karsten Albrecht1, Karsten Rauch1, Hermann A. Wegner1, Henning Hopf2, Lawrence T. Scott3, Lior Eshdat4, Ivan Aprahamian4 and Mordecai Rabinovitz4

1 Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany
2 Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
3 Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467-3860, USA
4 Department of Organic Chemistry, The Hebrew University of Jerusalem, Givat Ram, Jerusalem, 91904, Israel

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 [D8]-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-butylindeno)pyrene which disclose very interesting spectroscopic properties. In particular, tetrakis(tert-butylindeno)pyrene self-assembles in solution by way of π-stacking, and it can be reduced with potassium metal to a stable dianion, a readily dimerizing trianion radical, and a tetraanion.