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Synlett 2011(6): 745-769  
DOI: 10.1055/s-0030-1259919
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Coupling Reactions

Honghua Rao, Hua Fu*
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn;
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Publication History

Received 11 November 2010
Publication Date:
16 March 2011 (online)

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Abstract

This account summarizes our recent developments in copper-catalyzed coupling reactions, including copper-­catalyzed N-, O-, and P-arylations, the formation of carbon-nitrogen and carbon-carbon bonds via carbon-hydrogen bond activation, and the synthesis of N-heterocyclic compounds.

1 Introduction and Background

2 Copper-Catalyzed N-, O-, and P-Arylations

2.1 Copper-Catalyzed Synthesis of Primary Aromatic Amines

2.2 Copper-Catalyzed Synthesis of Phenols in Water

2.3 Copper-Catalyzed N-Arylation of Aliphatic Amines and Amino Acids at Room Temperature

2.4 Copper-Catalyzed N-Arylation of N-Heterocycles and Aliphatic Amines in Water

2.5 A General Ligand for Copper-Catalyzed N-, O-, and P-Aryl­ations

3 Copper-Catalyzed Formation of Carbon-Nitrogen and Carbon-Carbon Bonds via Carbon-Hydrogen Bond Activation

3.1 Copper-Catalyzed Amidation of sp³-Carbon-Hydrogen Bonds

3.2 Copper-Catalyzed Amidation of sp²-Carbon-Hydrogen Bonds of Aldehydes

3.3 Copper-Catalyzed Synthesis of Propargylamines via Carbon-Hydrogen Bond Activation

3.4 Copper-Catalyzed Aerobic Oxidative Couplings of Aromatic Boronic Acids with Terminal Alkynes

4 Copper-Catalyzed Synthesis of N-Heterocyclic Compounds

4.1 Copper-Catalyzed Cascade Synthesis of Quinazolinones

4.2 Copper-Catalyzed Cascade Synthesis of Isoquinolin-1(2H)-ones

4.3 Copper-Catalyzed Cascade Synthesis of 1,2,4-Benzothia­diazine 1,1-Dioxides

4.4 Copper-Catalyzed Cascade Synthesis of Quinazolines

4.5 Copper-Catalyzed Cascade Synthesis of Benzimidazoles

4.6 Copper-Catalyzed Cascade Synthesis of 2,5-Disubstituted Imidazolones

4.7 Copper-Catalyzed Cascade Synthesis of 2-Amino-1H-­indole-3-carboxylate Derivatives

4.8 Copper-Catalyzed Cascade Synthesis of Benzimidazo[1,2-b]isoquinolin-11-ones

4.9 Copper-Catalyzed Synthesis of Triazoles ‘on Water’

5 Summary

Key words

copper catalysis - arylations - cascade reactions - N-heterocycles - carbon-hydrogen bond activation