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

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Abstract

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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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.

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Key Words

Sandmeyer Reaction, Aryl Azides, Aryl Iodides, Ionic Liquids

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ID: J42-Y2008-0220