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Progress in Chemistry 2013, Vol. 25 Issue (11): 1898-1905 DOI: 10.7536/PC130149 Previous Articles   Next Articles

• Review •

Palladium- and Copper-Catalyzed Cross Coupling Reaction of Aliphatic Alcohols and Aryl Halides

Jin Xiaoping1*, Zhang Li3, Gao Haoqi2, Fang Jianghua2, Li Ruifeng3, Fang Yewen2,4*   

  1. 1. Department of Basic Education, Zhejiang Pharmaceutical College, Ningbo 315100, China;
    2. School of Chemical Engineering, Ningbo University of Technology, Ningbo 315016, China;
    3. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024;
    4. Ningbo Current Tech Fine Chemical Co. Ltd., Ningbo 315204, China
  • Received: Revised: Online: Published:
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Alkyl aryl ethers are present in many naturally occurring and medicinally relevant compounds. Palladium- and copper-catalyzed C—O bond formation reactions have become effective strategies for their preparation. Recent developments in palladium- and copper-catalyzed arylations of aliphatic alcohols are summarized in this review. Palladium-catalyzed C—O cross coupling of various aliphatic alcohols with aryl halides could be efficiently realized in the presence of di-tert-buthyl biarylphosphine ligand, di-tert-buthylphosphino pentaphenylferrocene ligand, or di-adamantyl-substituted Bippyphos ligand developed by Buchwald, Hartwig, and Beller groups respectively. With the copper catalyst, 1, 10-phenanthroline and its derivatives, β-dicarbonyl compounds were served as the most efficient ligands. Generally, palladium-catalyzed C—O cross-coupling reactions display mild reaction conditions, good functional-group compatability, and broad substrate scope compared to the copper catalyst system. Moreover, the difference of the two catalytic systems including the choice of ligand, reactivity, β-H elimination and mechanism is discussed. The design and synthesis of new ligands are the key point for the further development of the C—O cross coupling.

Contents
1 Introduction
2 Pd-catalzyed arylation of alphatic alcohols
3 Cu-catalyzed arylation of alphatic alcohols
3.1 Cu-catalyzed C—O cross coupling reaction without ligand
3.2 Cu-catalyzed C—O cross coupling reaction in the presence of ligand
4 Comparative studies of two catalysts
4.1 Choice of ligands
4.2 Catalytic activity
4.3 β-H elimination reaction
4.4 Reaction mechanism
5 Conclusion and outlook

Key words: alkyl aryl ethers, C—O cross coupling, Pd catalysis, Cu catalysis, ligands

CLC Number: 

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