Chem. J. Chinese Universities ›› 2014, Vol. 35 ›› Issue (6): 1236.doi: 10.7503/cjcu20130799

• Organic Chemistry • Previous Articles     Next Articles

Mild and Efficient Method for Synthesis of α-Halomethylketones

LIU Kaijian*()   

  1. Department of Materials and Chemical Engineering, Hunan Institute of Technology, Hengyang 421002, China
  • Received:2013-08-19 Online:2014-06-10 Published:2014-01-23
  • Contact: LIU Kaijian E-mail:liukaijian_1982@163.com
  • Supported by:
    † Supported by the Construct Program of the Key Discipline in Hunan Province, China and the Science and Technology Planning Project of Hunan Province, China(No. 2014FJ3053).

Abstract:

α-Halomethylketones are building blocks for the synthesis of various compounds due to their selective transformations with different reagents. Moreover, a wide range of α-halomethylketone derivatives attract increasing interests in pharmaceutical chemistry. α-Halomethylketones are also widespread used as intermediates in organic synthesis, such as in Favorskii rearrangement and Reformatsky reaction. However, their direct synthesis from the corresponding methylktones by N-halosuccinimides, molecular halogen and metal halides has been plagued by poor regioselectivity and over-halogenation. For the above reasons, a simple, convenient and environmentally benign protocol to synthesize the α-halomethylketones was developed by catalytic hydration of haloalkynes, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 3%(molar fraction) BrettPhosAuNTf2 and 3 mmol H2O in dichloroethane at room temperature, a broad range of haloalkynes were converted into α-halomethylketones in excellent yield through gold-catalyzed hydration reaction. The presented methodology will provide new strategies for α-halomethylketones-type drug design and synthesis, which has important academic significance and application value.

Key words: a-Halomethylketone, Haloalkyne, Gold-catalysis, Hydration reaction

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