Hydrofunctionalisation of an Aromatic Triphosphabenzene

Rosalyn L. Falconer, Dihao Zeng, Michael Green, Douglas W. Stephan, John E. McGrady*, Christopher A. Russell

*Corresponding author for this work

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Abstract

The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.
Original languageEnglish
Pages (from-to)12507-12511
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number54
Early online date15 Aug 2019
DOIs
Publication statusPublished - 25 Sep 2019

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Keywords

  • hydrofunctionalisation
  • hydrosilylation
  • metal-free synthesis
  • phosphorus
  • triphosphabenzene

Cite this

Falconer, R. L., Zeng, D., Green, M., Stephan, D. W., McGrady, J. E., & Russell, C. A. (2019). Hydrofunctionalisation of an Aromatic Triphosphabenzene. Chemistry - A European Journal, 25(54), 12507-12511. https://doi.org/10.1002/chem.201903229