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The Persistent Radical Effect in Organic Synthesis.

Dirk Leifert1, Armido Studer2,1

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149, Münster, Germany.

Angewandte Chemie (International Ed. in English)
|May 23, 2019
PubMed
Summary
This summary is machine-generated.

The persistent radical effect (PRE) enables selective cross-coupling of radicals with different lifetimes. This kinetic phenomenon enhances synthetic value by controlling radical reactions, expanding its applications in chemistry.

Keywords:
catalysiscross-couplingkineticsradicalstransition metals

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Area of Science:

  • Organic Chemistry
  • Chemical Kinetics
  • Synthetic Chemistry

Background:

  • Radical-radical couplings are typically diffusion-controlled, limiting selective cross-coupling of different radicals.
  • Achieving selective cross-coupling requires overcoming the challenge of rapid, non-selective radical reactions.

Purpose of the Study:

  • To explain the persistent radical effect (PRE) and its role in selective radical-radical cross-coupling.
  • To explore the scope and synthetic applications of PRE-mediated reactions.
  • To discuss radical stability, lifetimes, and their influence on coupling selectivity.

Main Methods:

  • Explanation of the persistent radical effect (PRE) based on kinetic principles.
  • Simulations of simple model systems to illustrate PRE mechanisms.
  • Summarization of synthetic examples involving PRE-mediated radical couplings.

Main Results:

  • PRE enables highly selective cross-coupling when radicals have different lifetimes and are generated at equal rates.
  • The PRE is effective even when coupling a longer-lived radical with a transient radical, broadening its applicability.
  • The review covers organic radical couplings and radical-metal crossover reactions.

Conclusions:

  • The persistent radical effect is a key kinetic phenomenon for achieving selective radical cross-coupling.
  • Understanding radical lifetimes is crucial for controlling reactivity and enhancing synthetic utility.
  • PRE-mediated reactions offer valuable synthetic transformations, including novel radical-metal interactions.