Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Practical Synthesis of 1,1-Difluoro- or 1-Fluoroalkenes from 2,2,2-Trifluoroacetophenone Derivatives

  • Received : 2011.03.16
  • Accepted : 2011.05.26
  • Published : 2011.08.20
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Abstract

Since the discovery of the fact that compounds bearing a vinylic fluoride moiety often exhibit remarkable biological activities such as enzyme inhibitors, many synthetic methods for fluorine-substituted vinylic compounds have been developed. The synthesis of selectively fluorinated building blocks, such as arylsubstituted fluoro-alkenes, also has become an area of interest in recent years. Herein we describe a novel and practical method for the synthesis of 1,1-difluoro- and 1-fluoroalkenes starting from easily accessible trifluoroacetophenone derivatives. Various 1,1-difluoro- and 1-fluoroalkenes were prepared by the reaction of the corresponding tosyl hydrazones that were derived from trifluoroacetophenone derivatives by treating with alkyl or aryllithium reagents via addition-elimination and single electron transfer (SET) mechanism.

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References

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