Premium
Preparation of Tröger Base Derivatives by Cross‐Coupling Methodologies
Author(s) -
Hof Fraser,
Schär Michael,
Scofield Denise M.,
Fischer Felix,
Diederich François,
Sergeyev Sergey
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590168
Subject(s) - chemistry , cyanation , combinatorial chemistry , supramolecular chemistry , intermolecular force , base (topology) , template , catalysis , covalent bond , surface modification , palladium , coupling reaction , fullerene , nanotechnology , molecule , organic chemistry , mathematical analysis , materials science , mathematics
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.