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PreprintCC BY-NC-NDChemRxiv

Synthesis of Quinoline- and Tetrahydroacridine-based SNN Ligands for Fe-catalyzed Olefin Hydrosilylation

  • Jeffrey N. Evenson1,2
  • Nathanael A. Taylor1,2
  • Travis A. Ferrin1,2
  • Emma L. Richardson1,2
  • Gregorio H. Villarreal-Quiroga1,2
  • Stacey J. Smith1,2
  • Mike S. Webster-Gardiner3
  • Julie A. Leseberg3
  • Brooke L. Small3
  • Rashmi Semwal1,4
  • Michael Findlater1,4
  • David J. Michaelis1,2
4 affiliations
  1. 1Department of Chemistry and Biochemistry
  2. 2Brigham Young University
  3. 3Kingwood Research & Technology Center
  4. 4University of California
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Abstract

We report the synthesis of a series of thio-iminoquinoline and thio-iminotetrahydroacridine SNN ligands for application in Fe-catalyzed hydrosilylation of olefins. In the hydrosilylation of styrene, the iminoquinoline ligands provide higher yields than the iminotetrahydroacridine derivatives. However, the acridine-based Fe catalysts have longer catalyst lifetimes and at low catalyst loadings (0.5 mol% Fe) provide higher turnover numbers (up to 2000 TON). The SNN-iron catalysts provide good yields in the hydrosilylation of both styrenyl and terminal olefins but fail to hydrosilylate 1,1- and 1,2- disubstituted styrenes, hindered and electron rich styrenes, or internal alkenes.

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Cite

BibTeXRIS
BibTeX
@misc{evenson2026synthesis,
  title = {{Synthesis of Quinoline- and Tetrahydroacridine-based SNN Ligands for Fe-catalyzed Olefin Hydrosilylation}},
  author = {Jeffrey N. Evenson and Nathanael A. Taylor and Travis A. Ferrin and Emma L. Richardson and Gregorio H. Villarreal-Quiroga and Stacey J. Smith and Mike S. Webster-Gardiner and Julie A. Leseberg and Brooke L. Small and Rashmi Semwal and Michael Findlater and David J. Michaelis},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008413/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008413/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Synthesis of Quinoline- and Tetrahydroacridine-based SNN Ligands for Fe-catalyzed Olefin Hydrosilylation
AU  - Jeffrey N. Evenson
AU  - Nathanael A. Taylor
AU  - Travis A. Ferrin
AU  - Emma L. Richardson
AU  - Gregorio H. Villarreal-Quiroga
AU  - Stacey J. Smith
AU  - Mike S. Webster-Gardiner
AU  - Julie A. Leseberg
AU  - Brooke L. Small
AU  - Rashmi Semwal
AU  - Michael Findlater
AU  - David J. Michaelis
PY  - 2026
DA  - 2026/09/07
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008413/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008413/v1
AB  - We report the synthesis of a series of thio-iminoquinoline and thio-iminotetrahydroacridine SNN ligands for application in Fe-catalyzed hydrosilylation of olefins. In the hydrosilylation of styrene, the iminoquinoline ligands provide higher yields than the iminotetrahydroacridine derivatives. However, the acridine-based Fe catalysts have longer catalyst lifetimes and at low catalyst loadings (0.5 mol% Fe) provide higher turnover numbers (up to 2000 TON). The SNN-iron catalysts provide good yields in the hydrosilylation of both styrenyl and terminal olefins but fail to hydrosilylate 1,1- and 1,2- disubstituted styrenes, hindered and electron rich styrenes, or internal alkenes.
ER  -