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Oxidative cross-coupling processes inspired by the Chan-Lam reaction.

Michael G J Doyle1, Rylan J Lundgren1

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|February 24, 2021
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Summary

Copper-catalyzed oxidative coupling reactions were developed to form carbon-carbon bonds, expanding the utility of Chan-Lam type reactions beyond traditional nitrogen and oxygen nucleophiles for synthesizing diverse organic molecules.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Chan-Lam reaction, a copper-catalyzed oxidative cross-coupling, is vital for synthesizing aniline and phenol derivatives using N- and O-nucleophiles with aryl boronic acids.
  • This reaction offers advantages like high chemoselectivity, mild conditions, and use of simple copper salts, presenting an alternative to palladium-catalyzed methods and aromatic substitutions.
  • However, a carbon-carbon bond-forming variant of the Chan-Lam reaction was previously undeveloped.

Purpose of the Study:

  • To discover and develop novel copper-catalyzed oxidative coupling reactions for carbon-carbon bond formation.
  • To extend the scope of Chan-Lam type reactions to include activated methylene derivatives and carboxylic acids as nucleophiles.
  • To explore the use of aryl boronic esters and amines as coupling partners in these new reactions.

Main Methods:

  • Exploration of copper-catalyzed oxidative coupling conditions.
  • Screening of various activated methylene compounds and carboxylic acids as nucleophiles.
  • Investigation of aryl boronic esters and amines as coupling partners.

Main Results:

  • Successful development of copper-catalyzed oxidative coupling reactions for C-C bond formation.
  • Demonstration of the coupling of activated methylene derivatives and carboxylic acids with aryl boronic esters and amines.
  • Expansion of the synthetic utility of Chan-Lam type reactions to C-C bond construction.

Conclusions:

  • The discovery of new Cu-catalyzed oxidative coupling reactions significantly broadens the applicability of Chan-Lam chemistry.
  • These novel methods provide efficient routes for synthesizing molecules with new carbon-carbon bonds.
  • The developed reactions offer valuable tools for organic synthesis, complementing existing methodologies.