Using solid catalysts in disulfide‐based dynamic combinatorial solution‐ and mechanochemistry

Ana M. Belenguer*, Adam A. L. Michalchuk, Giulio I. Lampronti, Jeremy K. M. Sanders*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

It was shown for the first time that solid amines can act as catalysts for disulfide-based dynamic combinatorial chemistry (DCC) by ball mill grinding. The mechanochemical equilibrium for the two disulfide reactions studied was reached within 1–3 h using ten different amine catalysts. This contrasts with the weeks to months to achieve solution equilibrium for most solid amine catalysts at 2 %mol mol −1 concentration in a 2 mMolar disulfide dynamic combinatorial library in a suitable solvent. The final mechanochemical equilibrium was independent of the catalyst used but varied with other ball mill grinding factors such as the presence of traces of solvent. The different efficiencies of the amines tested were discussed.

Original languageEnglish
Article numbere202102416
Number of pages7
JournalChemSusChem
Volume15
Issue number3
Early online date4 Dec 2021
DOIs
Publication statusPublished - 8 Feb 2022

Bibliographical note

Funding Information:
The authors acknowledge COST Action CA18112 – Mechanochemistry for Sustainable Industry. We thank: C. A. Bland for the mechanical and P. Donnelly for the software design of the automation of the grinders for repeat grinding; We thank the team from the mechanical workshop at the Department of Chemistry, University of Cambridge, for the manufacture of the jars; A.M.B. and J.K.M.S. thank Chris Hunter research team from the Department of Chemistry, University of Cambridge for general support. G.I.L. thanks the Department of Earth Sciences of the University of Cambridge for general support. The authors thank BAM IT for access to the required computational resources.

Publisher Copyright:
© 2021 Wiley-VCH GmbH.

Keywords

  • ball milling
  • disulfide exchange
  • dynamic covalent chemistry
  • mechanochemistry
  • solid amine catalysts

ASJC Scopus subject areas

  • Environmental Chemistry
  • General Chemical Engineering
  • General Materials Science
  • General Energy

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