Details
| Original language | English |
|---|---|
| Pages (from-to) | 1441-1448 |
| Number of pages | 8 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 7 |
| Publication status | Published - 20 Oct 2011 |
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 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.
Keywords
- Flow reactor, Inductive heating, Iodine azide, Polymer-supported reagents, Vinyl azides
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 7, 20.10.2011, p. 1441-1448.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed huisgen-type cycloaddition under inductive-heating conditions
AU - Kupracz, Lukas
AU - Hartwig, Jan
AU - Wegner, Jens
AU - Ceylan, Sascha
AU - Kirschning, Andreas
PY - 2011/10/20
Y1 - 2011/10/20
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.
AB - 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.
KW - Flow reactor
KW - Inductive heating
KW - Iodine azide
KW - Polymer-supported reagents
KW - Vinyl azides
UR - http://www.scopus.com/inward/record.url?scp=80055035713&partnerID=8YFLogxK
U2 - 10.3762/bjoc.7.168
DO - 10.3762/bjoc.7.168
M3 - Article
AN - SCOPUS:80055035713
VL - 7
SP - 1441
EP - 1448
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -