TY - JOUR A1 - Kupracz, Lukas A1 - Hartwig, Jan A1 - Wegner, Jens A1 - Ceylan, Sascha A1 - Kirschning, Andreas T1 - Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions JF - Beilstein Journal of Organic Chemistry PY - 2011/// VL - 7 SP - 1441 EP - 1448 SN - 1860-5397 DO - 10.3762/bjoc.7.168 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.7.168 KW - flow reactor KW - inductive heating KW - iodine azide KW - polymer-supported reagents KW - vinyl azides N2 - 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. ER -