Preparation of Tri- and Hexasubstituted Triptycene Synthons by Transition Metal Catalyzed Cross-Coupling Reactions for Post-Modifications.

Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans‐Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O.

Rational building strategies and appropriate synthons have been developed for the use of triptycene as a rigid presenting scaffold. Palladium-catalyzed cross-coupling reactions, such as Sonogashira and Suzuki couplings, were used to install a variety of different synthetic handles around the triptycene periphery in a high-yielding and controlled manner. These triptycene molecular handles were investigated for their potential in the construction of molecular arrays with defined spatial orientation e.g., for host-guest interactions or drug delivery systems. Such molecular synthons afforded expansion from the triptycene core by employing arm extension to increase the internal free volume characteristic of triptycene scaffolds for such applications. In addition, a range of mesogenic and glycosyl triptycene derivatives were achieved as a synthetic proof of concept for future work on potential drug delivery systems.

TRIPTYCENES; SONOGASHIRA reaction; SUZUKI reaction; SCAFFOLD proteins; GLYCOSYLATION

European Journal of Organic Chemistry, 2016, Vol 2016, Issue 1, p185

1434-193X

Academic Journal

10.1002/ejoc.201501272