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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:

A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008, 73, 316-319.

DOI: 10.1021/jo701937e


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

Fluorodediazonization in ionic liquid solvents: new life for the Balz-Schiemann reaction

K. K. Laali, V. J. Gettwert, J. Fluorine Chem., 2001, 107, 31-34.

Key Words

Sandmeyer Reaction, Aryl Azides, Aryl Iodides, Ionic Liquids

ID: J42-Y2008-0220