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tBu or not tBu?

Sten O Nilsson Lill1, Per Ryberg, Tobias Rein

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg, Kemigården 4, 412 96 Göteborg, Sweden. stenil@chem.gu.se

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Investigating palladium-catalyzed Heck coupling with phosphine ligands revealed a zigzag selectivity pattern. Computational methods, particularly M06-DFT, improved prediction accuracy, uncovering alternative mechanisms for bulky ligands.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Catalysis

Background:

  • Palladium-catalyzed Heck coupling is a vital C-C bond-forming reaction.
  • Regioselectivity in Heck reactions is influenced by ligand structure.
  • Understanding reaction mechanisms is key to optimizing catalytic processes.

Purpose of the Study:

  • To investigate the regioselectivity of the Heck coupling between aryl halides and ethyl vinyl ether using various phosphine ligands.
  • To evaluate the performance of different Density Functional Theory (DFT) methods in predicting selectivity.
  • To explore potential alternative reaction mechanisms for sterically demanding ligands.

Main Methods:

  • Experimental Heck coupling reactions with varying phosphine ligands (PPh(n)tBu(m)).
  • Computational studies using DFT methods (B3LYP and M06).
  • Analysis of reaction pathways and intermediate structures.

Main Results:

  • A zigzag selectivity pattern was observed with increasing tert-butyl substitution on the phosphine ligand.
  • M06-DFT functional provided a better description of selectivity trends compared to B3LYP.
  • Anionic mechanisms were identified for sterically demanding ligands (PtBu(3) and PPhtBu(2)), improving agreement between calculated and experimental selectivities.
  • A Halpern effect was observed, linking pre-complex stability to product abundance.

Conclusions:

  • Ligand structure significantly impacts regioselectivity in palladium-catalyzed Heck coupling.
  • Advanced DFT functionals like M06 are crucial for accurate mechanistic predictions.
  • Alternative reaction pathways, including anionic mechanisms, can operate, especially with bulky ligands.