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Copper-mediated oxidative direct C-C (hetero)aromatic cross-coupling.

Koji Hirano¹, Masahiro Miura

¹Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. k_hirano@chem.eng.osaka-u.ac.jp

Chemical Communications (Cambridge, England)

|September 20, 2012

Summary

Copper catalysts enable novel direct C-C cross-couplings for synthesizing complex molecules. These methods efficiently create heteroarylacetylenes and biaryls using readily available starting materials and atmospheric oxygen.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Traditional cross-coupling reactions often require expensive palladium catalysts and pre-functionalized substrates.
Development of efficient copper-mediated reactions offers a cost-effective and sustainable alternative for C-C bond formation.

Purpose of the Study:

To describe novel copper-mediated intermolecular oxidative direct C-C (hetero)aromatic cross-coupling reactions.
To develop efficient synthetic routes to heteroarylacetylenes, biaryls, and benzoheterocycles using copper catalysis.

Main Methods:

Utilized CuCl(2) salt and molecular oxygen for direct Sonogashira-type coupling of 1,3-azoles with terminal alkynes.
Employed a copper acetate complex for palladium-free direct biaryl coupling between 2-arylazines and 1,3-azoles.
Investigated copper-promoted annulative coupling of o-alkynylphenols/anilines with 1,3-azoles for benzoheterocycle synthesis.

Main Results:

Successfully synthesized various heteroarylacetylenes, including those derived from polyfluoroarenes.
Achieved direct biaryl coupling of azoles with arylazines and extended the methodology to indoles and pyrroles.
Developed a dehydrogenative approach to C3-azolylbenzoheterocycles and N-azolylindoles from non-halogenated precursors.

Conclusions:

Copper catalysis provides versatile and efficient pathways for direct C-C bond formation in (hetero)aromatic systems.
The developed methods offer sustainable alternatives, often utilizing atmospheric oxygen and avoiding palladium catalysts.
These protocols enable the synthesis of valuable heterocyclic compounds from readily accessible starting materials.