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Related Experiment Videos

Controlling the Scholl reaction.

Benjamin T King1, Jirí Kroulík, Charles R Robertson

  • 1Department of Chemistry, University of Nevada-Reno, Reno, Nevada 89557, USA. king@chem.unr.edu

The Journal of Organic Chemistry
|March 1, 2007
PubMed
Summary
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The Scholl reaction can be optimized for synthesizing complex molecules by controlling oligomerization with blocking groups. This study provides guidelines for its application in organic synthesis, particularly for substituted oligophenylenes.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The Scholl reaction is a key method for forming C-C bonds in aromatic systems.
  • Challenges exist in controlling selectivity and preventing side reactions like oligomerization.

Purpose of the Study:

  • To develop guidelines for the effective application of the Scholl reaction.
  • To understand and control the factors influencing Scholl reaction outcomes, particularly in oligophenylene synthesis.

Main Methods:

  • Utilized labeling experiments to investigate reaction pathways.
  • Employed blocking groups (e.g., t-butyl) to prevent product oligomerization.
  • Investigated the influence of directing groups on reaction regioselectivity.
  • Employed computational calculations (B3LYP/6-31G(d)) to elucidate reaction mechanisms.

Related Experiment Videos

  • Synthesized substituted o-terphenyl derivatives using Suzuki-Miyaura couplings.

    • Main Results:

    • The Scholl reaction fails in small, unsubstituted oligophenylenes due to product oligomerization.
    • Blocking groups effectively suppress oligomerization, enabling successful reactions.
    • Activating and deactivating groups direct bond formation predictably, with varying yields.
    • MoCl5 and PhI(OOCCF3)2/BF3.Et2O identified as effective reagents.
    • Computational studies suggest the reaction proceeds via arenium cations in alkoxyarenes.

    Conclusions:

    • Established guidelines for applying the Scholl reaction, enhancing its utility in organic synthesis.
    • Demonstrated the critical role of blocking groups in preventing oligomerization.
    • Provided insights into the mechanistic pathways and directing group effects governing the Scholl reaction.