Nucleophilic Fluorination

We have investigated the potential of BF3 and HBF4 as inexpensive and easily handled nucleophilic sources of fluorine. A range of substituted epoxides undergo efficient ring-opening hydrofluorination upon treatment with either BF3·OEt2 or HBF4 to give the corresponding syn- or anti-fluorohydrins. These valuable templates have been elaborated to a range of β-fluoroamphetamines and fluorinated natural product analogues.
 

Nucleophilic fluorination
 

Key Publications:

  1. Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for synthesis of benzylic fluorides
    Cresswell, A. J.; Davies, S. G.; Figuccia, A. L. A.; Fletcher, A. M.; Heijnen, D.; Lee, J. A.; Morris, M. J.; Kennett, A. M. R.; Roberts, P. M.; Thomson, J. E. Tetrahedron Lett. 201556, 3373
    [View Journal Page]
  2. Beyond the Balz-Schiemann reaction: the utility of tetrafluoroborates and boron trifluoride as nucleophilic fluoride sources
    Davies, S. G.; Roberts, P. M.; Cresswell, A. J.; Thomson, J. E. Chem. Rev. 2015115, 566
    [View Journal Page]
  3. Diastereodivergent hydroxyfluorination of allylic amines: application to the synthesis of 4-deoxy-4-fluoro-phytosphingosines
    Cresswell, A. J.; Davies, S. G.; Lee, J. A.; Morris, M. J.; Roberts, P. M.; Thomson, J. E. J. Org. Chem. 2012, 77, 7262 [View Journal Page]
  4. Ring opening hydrofluorination of α- and β-amino epoxides by HBF4: application to the asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol
    Cresswell, A. J.; Davies, S. G.; Lee, J. A.; Morris, M. J.; Roberts, P. M.; Thomson, J. E. J. Org. Chem. 2011, 76, 4617 [View Journal Page]
  5. β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
    Cresswell, A. J.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E.; Tyte, M. J. Org. Lett. 2010, 12, 2936 [View Journal Page]

 

 

 

 

 


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