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SET-induced biaryl cross-coupling: an S(RN)1 reaction.

Brandon E Haines1, Olaf Wiest

  • 1Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46556, United States.

The Journal of Organic Chemistry
|February 26, 2014
PubMed
Summary

The study introduces the first Grignard S(RN)1 reaction using SET-induced biaryl cross-coupling. A novel mechanism involving a transient Mg ion-radical cage intermediate is proposed, advancing organometallic chemistry understanding.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Reaction Mechanisms

Background:

  • Grignard reagents are fundamental in organic synthesis.
  • Radical nucleophilic substitution (S(RN)1) reactions offer unique synthetic pathways.
  • Understanding reaction intermediates is crucial for mechanistic elucidation.

Purpose of the Study:

  • To establish the first example of a Grignard S(RN)1 reaction.
  • To investigate the mechanism of SET-induced biaryl cross-coupling reactions involving Grignard reagents.
  • To propose a new mechanistic pathway based on experimental and computational data.

Main Methods:

  • Utilized SET-induced biaryl cross-coupling reaction conditions.
  • Employed Density Functional Theory (DFT) calculations.
  • Conducted trapping experiments to detect reaction intermediates.

Main Results:

  • Established the SET-induced biaryl cross-coupling as the first Grignard S(RN)1 reaction.
  • DFT calculations revealed a transient Mg ion-radical cage intermediate.
  • Trapping experiments failed to detect the radical intermediate due to its rapid reaction.

Conclusions:

  • The reaction proceeds via a novel mechanism involving a short-lived radical intermediate.
  • A new mechanism for Grignard S(RN)1 reactions is proposed.
  • This work expands the scope and mechanistic understanding of Grignard reagent reactivity.