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Supramolecular construction of a cyclobutane ring system with four different substituents in the solid state
Journal article   Open access   Peer reviewed

Supramolecular construction of a cyclobutane ring system with four different substituents in the solid state

Michael A Sinnwell, Ryan H Groeneman, Benjamin J Ingenthron, Changan Li and Leonard R MacGillivray
Communications chemistry, Vol.4(1), pp.1-7
05/10/2021
DOI: 10.1038/s42004-021-00493-3
PMCID: PMC9814370
PMID: 36697559
url
https://doi.org/10.1038/s42004-021-00493-3View
Published (Version of record) Open Access

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Abstract

AbstractMethods to form cyclobutane rings by an intermolecular [2 + 2] cross-photoreaction (CPR) with four different substituents are rare. These reactions are typically performed in the liquid phase, involve multiple steps, and generate product mixtures. Here, we report a CPR that generates a cyclobutane ring with four different aryl substituents. The CPR occurs quantitatively, without side products, and without a need for product purification. Generally, we demonstrate how face-to-face stacking interactions of aromatic rings can be exploited in the process of cocrystallization and the field of crystal engineering to stack and align unsymmetrical alkenes in CPRs to afford chiral cyclobutanes with up to four different aryl groups via binary cocrystals. Overall, we expect the process herein to be useful to generate chiral carbon scaffolds, which is important given the presence of four-membered carbocyclic rings as structural units in biological compounds and materials science.

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