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.
DOI: 10.1021/jo701937e (free Supporting Information)
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.
see article for more examples
K. K. Laali, V. J. Gettwert, J. Fluorine Chem., 2001, 107, 31-34.