Multistep Flow Synthesis of Vinyl Azides and their use in the Copper-Catalyzed Huisgen-type Cycloaddition under Inductive-Heating Conditions
The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in good yield. The third step involves the formation of vinyl triazoles by a copper-catalyzed Huisgen-"click" cycloaddition. The required heat is generated by electromagnetic induction based on copper. Copper serves both as heatable as well as catalytically active packed-bed material inside the flow reactor.
The article is published online ion Beilstien Journal of Organic Chemistry and is free to access.