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Progress in Chemistry 2018, Vol. 30 Issue (5): 564-577 DOI: 10.7536/PC171132 Previous Articles   Next Articles

• Review •

C—C and C-Heteroatom Bonds Formation Based on Oxidative Dehydrogenation of Cyclohexanones

Jinjin Chen, Dan Chang, Fuhong Xiao, Guojun Deng*   

  1. College of Chemistry, Xiangtan University, Xiangtan 411105, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21372187).
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Cyclohexanones are cheap and commercially available compounds and widely used as raw materials and key intermediates in organic synthesis. Dehydrogenative aromatization has emerged as an efficient approach to access functionalized arenes. The transformation commonly involves sequential nucleophilic addition, dehydration and catalytically oxidative dehydrogenation. Compared to the traditional arylation methods, this strategy avoids the use of harsh reaction conditions and the production of halide wastes. In addition, the chemo-and regioselectivities can be easily controlled. Therefore, this method offers a milder/greener means for the synthesis of functionalized arenes. This review mainly focuses on the direct formation of C—C and C-heteroatom bonds using cyclohexanones as raw materials and the extension of these methodologies to the construction of various heterocycles.
Contents
1 Introduction
2 Oxidative dehydrogenation of cyclohexanones
3 C—C bond formation based on cyclohexanones
4 C-heteroatom bond formation based on cyclohexanones
4.1 C—O bond formation
4.2 C—S bond formation
4.3 C—N bond formation
4.4 Construction of heterocycles based on the formation of C-heteroatom bond
5 Conclusion and outlook
Key words: cyclohexanones, dehydrogenative aromatization, C—C bond, C-heteroatom bond, heterocycles

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