Abstract
Derivatives of the Tröger 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 Tröger 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.
Original language | English (US) |
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Pages (from-to) | 2333-2344 |
Number of pages | 12 |
Journal | Helvetica Chimica Acta |
Volume | 88 |
Issue number | 8 |
DOIs | |
State | Published - 2005 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Biochemistry
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry