Mechanochemical Route to Upper Rim Tetrafunctionalised Prochiral and Inherently Chiral Calix[4]arenes

Bew, Sean P., Stephenson, G. Richard, Horil Roy, Deeptee, Gardiner, William and Martinez Lozano, Luis (2025) Mechanochemical Route to Upper Rim Tetrafunctionalised Prochiral and Inherently Chiral Calix[4]arenes.

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Abstract

The application of an experimentally straightforward synthesis of upper rim tetrafunctionalised prochiral ABAB (AB ≠ H), ABBB (AB ≠ H), ABCB (ABC ≠ H) and inherently chiral, racemic calix[4]arenes (ABCD ≠ H) calix[4]arenes using a pestle and mortar as the ‘reaction flask'. These, till now, difficult-to-source modalities are generated via a combination of mechanochemistry, Cannizzaro and Suzuki-Miyaura or Sonogashira couplings which transform a simple to synthesise calix[4]arene starting material into structure and function diverse prochiral (i.e. ABCB) and racemic, inherently chiral ABCD cone-confined calix[4]arenes. Exploiting this methodology and filling an important ‘gap' in calix[4]arene chemistry, we report the first examples of ABCD calix[4]arenes appended with four different C-substituents (i.e. ABCD ≠ H) on the upper rim.

Item Type: Article
Uncontrolled Keywords: calixarene,inherent chirality,mechanochemistry,transition metal catalysis,redox chemistry
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups: Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User: LivePure Connector
Date Deposited: 10 Jul 2025 14:30
Last Modified: 10 Jul 2025 14:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/99880
DOI: 10.26434/chemrxiv-2025-nzqg3

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