Continuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction

• Melanie Kitchin^ab
• Kristina Konstas^a
• Christopher J. Sumby^b
• Milena L. Czyz^a
• Peter Valente^b
• Matthew R. Hill^*ab
• Anastasios Polyzos^*ac
• Christian J. Doonan^*ab

• ^* Corresponding authors
• ^a CSIRO Manufacturing Flagship, Bayview Avenue, Clayton, Australia
• ^b Centre for Advanced Nanomaterials and the School of Physical Sciences, The University of Adelaide, Adelaide, Australia

The facile synthesis of the cage molecule (C110H56Br2) via a remarkable three-fold homo-coupling macrocyclization reaction using continuous flow methodology is reported. Synthesis via continuous flow chemistry improves the residence time, safety, and environmental profile of this synthetically challenging reaction. Further, the new cage possesses halogen atoms at its apex that serve to expand the potential reaction space of these intrinsically porous, all carbon–carbon bonded molecular cage molecules.

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