Continuous, stable, and safe organometallic reactions in flow at room temperature assisted by deep eutectic solvents

Florian F. Mulks, Bruno Pinho, Andrew W.j. Platten, M. Reza Andalibi, Antonio J. Expósito, Karen J. Edler, Eva Hevia, Laura Torrente-Murciano

Research output: Contribution to journalArticlepeer-review

Abstract

This work demonstrates the first continuous, stable, and safe operation of organometallic reactions in flow under ambient conditions with high moisture tolerance and clogging resistance. The addition of deep eutectic solvents (DESs), such as glyceline (choline chloride/glycerol) and reline (choline chloride/urea), overcomes the previous limitations associated with the need for cryogenic conditions (long residence times and high energy requirements) and clogging. The immiscibility of the different solvents leads to a segmented flow where the reactive organic substrates are dispersed in a continuous DES-containing carrier phase. This system provides intimate contact between solvents, favoring the dissolution of lithium species (by-product) into the DES phase, avoiding the clogging under a wide range of conditions. In addition, the microfluidic scale provides excellent heat management (recirculation flow patterns) and a high surface area/volume ratio, enabling safe operation. The benefits of DESs were studied with a selection of two organolithiums and two organomagnesium reagents, and different imine/ketone substrates.

Original languageEnglish
Pages (from-to)3382-3394
Number of pages13
JournalChem
Volume8
Issue number12
DOIs
Publication statusPublished - 8 Dec 2022

Keywords

  • SDG11: Sustainable cities and communities
  • SDG9: Industry innovation and infrastructure
  • deep eutectic solvents
  • flow reactors
  • green chemistry
  • green solvents
  • multi-phase flow
  • organometallic reactions
  • room temperature

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

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