Jump to main content
Jump to site search

Issue 10, 1997
Previous Article Next Article

Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling

Abstract

High yields of the mixed perfluorinated biaryls (C6F5–Ar) are obtained by the catalytic dediazoniation of the pentafluorobenzenediazonium salt (C6F5N2+BF4) in acetonitrile solutions containing various aromatic substrates (ArH) together with small amounts of iodide salts. Activated (electron-rich) as well as deactivated (electron-poor) arenes are successfully pentafluorophenylated by this method. The arylation is distinct from the azo coupling of the same substrates, which takes place in the absence of the iodide catalyst and yields the corresponding diazene (C6F5N[double bond, length half m-dash]N–Ar) as product. The catalytic role of iodide, and the isomeric product distributions obtained with this procedure indicate that the arylation proceeds via the pentafluorophenyl radical in a efficient homolytic chain process. Since azo coupling involves electrophilic aromatic substitution of electron-rich ArH by C6F5N2+, the two competing pathways are distinct and do not have reactive intermediates in common.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 2, 1997, 2003-2012
Article type
Paper

Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling

D. Kosynkin, T. Michael Bockman and J. K. Kochi, J. Chem. Soc., Perkin Trans. 2, 1997, 2003 DOI: 10.1039/A701745F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Search articles by author

Spotlight

Advertisements