Continuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction
Melanie Kitchin, Kristina Konstas, Christopher J Sumby, Milena L Czyz, Peter Valente, Matthew R Hill, Anastasios Polyzos, Christian J Doonan
Chemical Communications | ROYAL SOC CHEMISTRY | Published : 2015
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.
Awarded by Australian Research Council
C.J.D. and C.J.S. would like to acknowledge the Australian Research Council for funding (DP120103909 (C.J.D.), FT100100400 (C.J.D.), and FT0991910 (C.J.S.)). A.P would like to acknowledge CSIRO OCE Julius Award for funding. Parts of this work were funded by the Science Industry and Endowment Fund. Aspects of this research were undertaken on the MX1 beamline at the Australian Synchrotron, Victoria, Australia. Dr Campbell Coghlan is thanked for collecting and solving X-ray crystallographic data on Cage C2.