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π-Complexation in nickel-catalyzed cross-coupling reactions.

S Kyle Sontag1, Jenna A Bilbrey, N Eric Huddleston

  • 1Department of Chemistry, ‡Center for Computational Chemistry, and §College of Engineering, University of Georgia , Athens, Georgia 30602, United States.

The Journal of Organic Chemistry
|February 5, 2014
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Summary

The kinetic isotope effect (KIE) reveals the initial step in nickel-catalyzed oxidative addition to haloarenes involves irreversible π-complexation. This study clarifies the mechanism for these important organometallic reactions.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Oxidative addition is a key step in many catalytic cycles.
  • Understanding the initial steps is crucial for catalyst design.
  • Nickel catalysts are versatile in organic synthesis.

Purpose of the Study:

  • To determine the rate-limiting step in the oxidative addition of zerovalent nickel to haloarene substrates.
  • To investigate the role of π-complexation in the reaction mechanism.
  • To elucidate the mechanism using experimental and computational methods.

Main Methods:

  • Experimental kinetic isotope effect (KIE) studies.
  • Density functional theory (DFT) computations.
  • Analysis of haloarene substrates including o-methylbenzene, dimethoxybenzene, and thiophene derivatives.

Main Results:

  • The kinetic isotope effect (KIE) indicates that the first irreversible step is π-complexation.
  • DFT calculations confirm the stability of η(2)-bound π-complexes.
  • Ring-walking of the Ni(0) catalyst and subsequent oxidative addition are predicted to be facile.

Conclusions:

  • The study experimentally and computationally confirms π-complexation as the initial irreversible step in the oxidative addition of Ni(0) to haloarenes.
  • The findings provide insights into the mechanism of nickel-catalyzed C-X bond activation.
  • This work contributes to the development of more efficient catalytic systems.