Preparation of Tröger base derivatives by cross-coupling methodologies

Fraser Hof, Michael Schär, Denise M. Scofield, Felix Fischer, François Diederich, Sergey Sergeyev

Research output: Contribution to journalReview article

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 languageEnglish (US)
Pages (from-to)2333-2344
Number of pages12
JournalHelvetica Chimica Acta
Volume88
Issue number8
DOIs
StatePublished - Sep 9 2005
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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  • Cite this

    Hof, F., Schär, M., Scofield, D. M., Fischer, F., Diederich, F., & Sergeyev, S. (2005). Preparation of Tröger base derivatives by cross-coupling methodologies. Helvetica Chimica Acta, 88(8), 2333-2344. https://doi.org/10.1002/hlca.200590168