Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF6] Ionic Liquid
Abigail Hubbard, Takao Okazaki and Kenneth K. Laali*
*Department of Chemistry, Kent State University, Kent, Ohio 44242, Email: klaalikent.edu
A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008, 73, 316-319.
Reaction of [ArN2][BF4] salts immobilized in [BMIM][PF6] ionic liquid (IL) with TMSI and TMSN3 represents an efficient method for the preparation of iodo- and azido-derivatives via dediazoniation. Using TMSBr, competing fluorodediazoniation (ArF formation) and hydrodediazoniation (ArH formation) were observed depending on the substituents on the benzenediazonium cation.
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K. K. Laali, V. J. Gettwert, J. Fluorine Chem., 2001, 107, 31-34.