The First Stable Diazonium Ion on Solid Support—Investigations on Stability and Usage as Linker and Scavenger in Solid-Phase Organic Synthesis
Nitrogen-Based Linkers, Part 8. This work was supported by the Fonds der Chemischen Industrie (Liebig-Stipend to S.B.) and the Deutsche Forschungsgemeinschaft (BR1750-1). We thank Prof. Dr. D. Enders for the generous support of our work. The companies BASF AG, Bayer AG, Degussa-Hüls AG, and Calbiochem-Novabiochem AG are acknowledged for donations of chemicals and Grünenthal GmbH for financial support. For DSC measurements we also thank Prof. Dr. Franz-Josef Wortmann and Dr. Numan Özgün at the Deutsches Wollforschungsinstitut (DWI) at the RWTH Aachen. Part 7: M. Lormann, S. Dahmen, S. Bräse, Tetrahedron Lett. 2000, 41, 3813–3816.
Abstract
Stability instead of explosiveness characterizes a novel diazonium ion T2* on a solid support, which opens a facile route to the versatile chemistry of diazo compounds and triazenes. This diazonium ion can be used as a linker for the immobilization and modification of amines (see scheme). The high stability also allows its application as a scavenger for amines, anilines, and phenols in combinatorial synthesis in the liquid phase.
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