Preparation of Troger Base Derivatives by Cross-Coupling Methodologies

Derivatives of the Troger base are finding increasing application in supramolecular chemistry: they are introduced as rigid scaffolds into synthetic receptors and 'molecular torsional balances' to quantify weak intermolecular interactions, and serve as efficient 'covalent templates' in the tether-directed remote functionalization of fullerenes. This paper describes the facile synthesis of symmetrically (Schemes 1 and 2) and unsymmetrically (Schemes 4 and 5) substituted Troger base derivatives starting from the corresponding, readily available dihalo compounds. A variety of metal-catalyzed cross-coupling reactions, including Suzuki couplings, palladium-catalyzed cyanation and boronation, and copper-catalyzed amidations are used to achieve these transformations. © 2005 Verlag Helvetica Chimica Acta AG.

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