Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

L Kupracz, J Hartwig, J Wegner…

Index: Kupracz, Lukas; Hartwig, Jan; Wegner, Jens; Ceylan, Sascha; Kirschning, Andreas Beilstein Journal of Organic Chemistry, 2011 , vol. 7, p. 1441 - 1448

Full Text: HTML

Citation Number: 41

Abstract

Abstract 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 ...