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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Base-Induced Radical Carboamination of Nonactivated Alkenes with Aryldiazonium Salts
Stephanie Kindt1, Karina Wicht1, Markus R Heinrich1
1Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg , Schuhstraße 19, 91052 Erlangen, Germany.
Abstract:
A new transition-metal-free version of the Meerwein arylation has been developed. The key feature of this carboamination-type reaction is the slow base-controlled generation of aryl radicals from aryldiazonium tetrafluoroborates, so that a sufficient quantity of diazonium ions remains to enable efficient trapping of the alkyl radical adduct resulting from aryl radical addition to the alkene. Under strongly basic conditions, diazoanhydrides are likely to take over the role of the nitrogen-centered radical scavengers.
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