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Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
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Dual Gold Catalysis: Stepwise Catalyst Transfer via Dinuclear Clusters.

Mie Højer Larsen1,2, K N Houk1, A Stephen K Hashmi2,3

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|August 11, 2015
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Dual gold catalysts are increasingly used, but their transfer mechanism remains unclear. This study reveals a stepwise dual catalyst transfer as the lowest energy pathway for dibenzopentalene synthesis, enabling further reactions.

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Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Organic Synthesis

Background:

  • Dual gold catalysts are gaining traction in organic synthesis, yet the mechanistic details of catalyst transfer and its impact on reaction efficiency are poorly understood.
  • Understanding these mechanisms is crucial for optimizing catalytic processes and developing new synthetic methodologies.

Purpose of the Study:

  • To computationally investigate the mechanism of intermolecular catalyst transfer in the synthesis of dibenzopentalene from a specific diyne precursor.
  • To compare the energy profiles of single catalyst transfer (direct and water-mediated) versus dual catalyst transfer.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to explore reaction pathways.
  • Transition states for each step of the proposed catalytic cycles were identified and characterized.
  • Energetic comparisons were made between different proposed transfer mechanisms.

Main Results:

  • Three distinct mechanistic scenarios were evaluated: single transfer from monoaurated complex, water-mediated single transfer, and dual transfer from diaurated complex.
  • Transition structures were successfully located for all investigated steps.
  • A stepwise dual catalyst transfer pathway was identified as the energetically most favorable route.

Conclusions:

  • The study elucidates a novel three-step mechanism for the transfer of two gold moieties from a dibenzopentalene product to a diyne substrate.
  • This dual transfer mechanism directly yields a σ,π-gold coordinated diyne intermediate, poised for subsequent intramolecular cyclization.
  • The findings provide critical mechanistic insights into dual gold catalysis, essential for enhancing turnover frequency and synthetic utility.