Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 1441-1448Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.168
Keywords
flow reactor; inductive heating; iodine azide; polymer-supported reagents; vinyl azides
Categories
Funding
- Fonds der Chemischen Industrie
- Henkel AG & Co. KGaA (Dusseldorf, Germany),
- Evonik Degussa GmbH (Essen, Germany)
- IFF GmbH (Munchen, Germany)
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The multistep flow synthesis of vinyl azides and their application in the synthesis of vinyltriazoles is reported. 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.
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