Preparation of Tri‐ and Hexasubstituted Triptycene Synthons by Transition Metal Catalyzed Cross‐Coupling Reactions for Post‐Modifications. Issue 1 (2nd December 2015)

• Record Type: Journal Article
• Authors: Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans‐Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O.
• Is Part Of: European journal of organic chemistry. Issue 1(2016)
• Page Start: 185
• Page End: 195
• Publication Date: 2015-12-02
• Subjects: Synthetic methods -- C–C coupling -- Cycloaddition -- Polycycles -- Triptycene; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501272
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : Rational building strategies and appropriate synthons were developed for the use of triptycene as a rigid hexafunctional‐presenting scaffold with defined spatial orientation. One‐pot, sixfold palladium catalyzed cross‐coupling Sonogashira‐ and Suzuki‐style reactions allow facile introduction of a variety of different synthetic handles at the 2, 3, 6, 7, 14, 15‐positions.