Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

Gwilherm Evano*†, Nicolas Blanchard*‡ and Mathieu Toumi†
Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France, and Laboratoire de Chimie Organique, Bioorganique et Macromoléculaire, UMR CNRS 7015, ENSCMu, Université de Haute-Alsace, 3 rue A. Werner, 68093 Mulhouse Cedex, France
Chem. Rev., 2008, 108 (8), pp 3054–3131
DOI: 10.1021/cr8002505
Publication Date (Web): August 13, 2008
Copyright © 2008 American Chemical Society
* Authors to whom correspondence should be addressed (evano@chimie.uvsq.fr, nicolas.blanchard@uha.fr)., †

Université de Versailles Saint Quentin en Yvelines.

, ‡

Université de Haute-Alsace.

This article is part of the Coinage Metals in Organic Synthesis special issue.
General Organic Chemistry

Table of Contents

  • 1. Introduction
  • 2. Background: Copper-Mediated Coupling Reactions
    • 2.1. Ullmann, Goldberg, and Hurtley Coupling Reactions
    • 2.2. Available Copper-Based Systems
    • 2.3. C−N Bond Formation
      • 2.3.1. Arylation of Arylamines
      • 2.3.2. Arylation of Alkylamines
      • 2.3.3. Arylation of Amides, Imides, and Carbamates
      • 2.3.4. Arylation of N-Heterocycles
      • 2.3.5. Synthesis of Enamides
      • 2.3.6. Synthesis of Ynamides and Allenamides
    • 2.4. C−O Bond Formation
      • 2.4.1. Arylation of Phenols
      • 2.4.2. Arylation of Aliphatic Alcohols
      • 2.4.3. Synthesis of Enol Ethers by Vinylation of Alcohols
      • 2.4.4. Synthesis of Oxygenated Heterocycles by Intramolecular Vinylation of Alcohols
      • 2.4.5. Synthesis of Oxygenated Heterocycles by Intramolecular O-Vinylation or O-Arylation of Ketones and Amides
      • 2.4.6. Synthesis of Benzopyranones by Intramolecular Arylation of Benzoic Acids
    • 2.5. C−I Bond Formation: Aromatic Finkelstein Reaction
    • 2.6. C−C Bond Formation
      • 2.6.1. Synthesis of Biaryls
      • 2.6.2. Synthesis of Aryl−Alkynes
      • 2.6.3. Synthesis of Ene−Ynes
      • 2.6.4. Synthesis of 1,3-Dienes
      • 2.6.5. Synthesis of Aryl−Alkenes
      • 2.6.6. Synthesis of 1,n-Diynes
      • 2.6.7. Coupling Reactions of α-Hydroxystannanes
      • 2.6.8. Cyanation of Aromatic, Rosenmund−von Braun Reaction
      • 2.6.9. C-Arylation Reactions of CH-Acid Derivatives: Hurtley Reaction
      • 2.6.10. Methylenation Reaction
  • 3. Natural Product Total Synthesis: Formation of C−N Bonds
    • 3.1. Arylation of Alkylamines
    • 3.2. Arylation of Amides and Carbamates
    • 3.3. Arylation of N-Heterocycles
    • 3.4. Enamides
    • 3.5. Ynamides and Allenamides
    • 3.6. Intramolecular Reactions
      • 3.6.1. Formation of Small- to Medium-Sized Nitrogen Heterocycles
      • 3.6.2. Intramolecular C−N Cross-Coupling Reactions as Macrocyclization Procedures
  • 4. Natural Product Total Synthesis: Formation of C−O Bonds
    • 4.1. Arylation of Phenols
    • 4.2. Arylation of Alcohols
    • 4.3. Enol Ethers
    • 4.4. Intramolecular Reactions
      • 4.4.1. Formation of Small- to Medium-Sized Oxygenated Heterocycles
      • 4.4.2. Intramolecular C−O Cross-Coupling Reactions as Macrocyclization Procedures
  • 5. Natural Product Total Synthesis: Aromatic Finkelstein Reaction
  • 6. Natural Product Total Synthesis: Formation of C−C Bonds
    • 6.1. Biaryls
      • 6.1.1. Biaryls by Classical Ullmann Cross-Coupling
      • 6.1.2. Biaryls by Oxidative Coupling of Phenols
    • 6.2. Ene−Ynes
    • 6.3. 1,3-Dienes
      • 6.3.1. 1,3-Dienes by CuTC-Promoted Stille-Type Cross-Coupling
      • 6.3.2. 1,3-Dienes by Stille-Type Cross-Coupling: Use of CuTC as an Additive
    • 6.4. Polyynes
    • 6.5. Using α-Hydroxy Stannanes
    • 6.6. Using the Hurtley Reaction
    • 6.7. Using a Methylenation Reaction
  • 7. Conclusions and Future Prospects
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History

  • Published In Issue August 13, 2008
  • Article ASAPAugust 13, 2008
  • Received: July 07, 2007

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