Insights into mechanism and selectivity in ruthenium(II)-catalysed ortho-arylation reactions directed by Lewis basic groups

Jamie McIntyre, Irene Mayoral-Soler, Pedro Salvador Sedano, Albert Poater, David James Nelson

Research output: Contribution to journalArticle

12 Citations (Scopus)
11 Downloads (Pure)

Abstract

We report a detailed study of the selectivity of ruthenium-catalysed C-H arylation reactions directed by Lewis basic heterocycles. A reactivity scale for directing power in these reactions, based on the results of intermolecular competition experiments, is reported for the first time. Our work is supported by detailed density functional theory calculations that reveal the underlying mechanism of this reaction, which requires the dissociation of a p-cymene ligand before oxidative addition becomes competent. The calculated energetic span of the catalytic cycles for each substrate is broadly in agreement with our experimental observations. This work advances our understanding of mechanism and selectivity in these reactions, and provides a basis for future catalyst design efforts.
Original languageEnglish
JournalCatalysis Science and Technology
Early online date1 Jun 2018
DOIs
Publication statusE-pub ahead of print - 1 Jun 2018

Keywords

  • ruthenium-catalysed C-H arylation
  • Lewis basic heterocycles
  • density functional theory calculations
  • catalytic cycles

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    Student Theses

    A quantitative scale for directing group power in ruthenium(II)-catalysed ortho-directed C-H arylation reactions

    Author: McIntyre, J., 12 Oct 2017

    Supervisor: Nelson, D. (Supervisor) & Murphy, J. (Supervisor)

    Student thesis: Master's Thesis

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