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Updated: Mar 3, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Synthesis of Dicarba-closo-dodecaborane-1-carboxamides
Matthias S Scholz1, Lukas M Wingen1
1Pharmaceutical Institute, University of Bonn , An der Immenburg 4, D-53121 Bonn, Germany.
Abstract:
Amide bond formation is one of the most important chemical reactions. In peptide and organic chemistry, the application of amide coupling reagents is a routine strategy, but surprisingly not in carborane chemistry. Thus, we now report a fast, safe, and robust protocol to couple amines to m- and p-dicarba-closo-dodecaborane-1-carboxylic acids. The procedure comprises the activation of carboxylic acid with the coupling reagent (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)(dimethylamino)morpholinocarbenium hexafluorophosphate, extraction of the product using the hydrophobic nature of the cluster, and a straightforward chromatographic purification. The protocol allows access to a variety of carborane-organic hybrid molecules suitable for application in multiple areas.
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