Self-Propagated para-Fluoro-Thiol Reaction

Federica Cavalli; Fabian R Bloesser; Christopher Barner-Kowollik; Leonie Barner

doi:10.1002/chem.201901290

Self-Propagated para-Fluoro-Thiol Reaction

Chemistry. 2019 Aug 1;25(43):10049-10053. doi: 10.1002/chem.201901290. Epub 2019 Jul 8.

Authors

Federica Cavalli¹, Fabian R Bloesser², Christopher Barner-Kowollik^{2

3

4}, Leonie Barner^{1

2

4}

Affiliations

¹ Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
² School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, Brisbane, QLD, 4000, Australia.
³ Macromolecular Architectures, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128, Karlsruhe, Germany.
⁴ Institute for Future Environments, Queensland University of Technology (QUT), 2 George Street, Brisbane, QLD, 4000, Australia.

PMID: 31190342
DOI: 10.1002/chem.201901290

Abstract

We introduce a protecting-group-free concept for the powerful para-fluoro-thiol reaction (PFTR) employing a source of fluoride ions as base. The reaction is shown to be self-propagating, with under-stoichiometric amounts of base, thus effectively foregoing the need for high base concentrations. Careful tuning of the solvent-thiol combination allows for quantitative conversion, in some cases within a short timeframe, when only minimal amounts of base are used, allowing the PFTR reaction to essentially proceed base-free.

Keywords: base; fluorine; para-fluoro thiol; self-sustained; synthetic methods.

Abstract

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