Synthesis 2025; 57(21): 3211-3226
DOI: 10.1055/a-2640-7616
Paper
Published as part of the Special Topic Dedicated to Prof. Paul Knochel

Hexafluoroisopropanol-Promoted Substitution Toward the Synthesis of Enantiopure Ferrocene Phosphines

Authors

  • Sirine Boussandel

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)
    2   Laboratory of Hetero-Organic Compounds and Nanostructured Materials, University of Carthage, Tunis, Tunisia (Ringgold ID: RIN61796)
  • William Erb

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)
  • Thierry Roisnel

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)
  • Marielle Blot

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)
  • Jean-Pierre Hurvois

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)
  • Ian Butler

    3   School of Computer Science and Electronic Engineering, Bangor University, Bangor, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1506)
  • Ali Samarat

    2   Laboratory of Hetero-Organic Compounds and Nanostructured Materials, University of Carthage, Tunis, Tunisia (Ringgold ID: RIN61796)
  • Florence Mongin

    1   Institut des Sciences Chimiques de Rennes, Université de Rennes, Rennes, France (Ringgold ID: RIN27079)

Supported by: University of Carthage
Supported by: Tunisian Ministry of Higher Education and Scientific Research
Supported by: Université de Rennes
Supported by: Centre National de la Recherche Scientifique
Funding Information This work was supported by the Université de Rennes, the Centre National de la Recherche Scientifique, the University of Carthage, and the Tunisian Ministry of Higher Education and Scientific Research (grant for S.B.).


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Abstract

Enantiopure ferrocene-based phosphorus derivatives represent an important class of compounds with multiple applications in organic synthesis and coordination chemistry. Here, we report how the use of hexafluoroisopropanol can favor pseudo-benzylic substitutions toward both bulky diphosphine ligands and phosphonate derivatives. While the former can be involved in the formation of metal complexes, the latter can be easily reduced to original enantiopure ferrocenic primary mono- and diphosphines.

Supplementary Material



Publication History

Received: 16 May 2025

Accepted after revision: 20 June 2025

Accepted Manuscript online:
20 June 2025

Article published online:
15 August 2025

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