Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen

A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes...

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Published inOrganic & biomolecular chemistry Vol. 12; no. 21; pp. 3340 - 3343
Main Authors Chen, Huoji, Yang, Wanfei, Wu, Wanqing, Jiang, Huanfeng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.06.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
TRANSFORMATION
AEROBIC OXIDATIVE AMINATION
SERIAL LIGAND CATALYSIS
ALKYLATION
CARBOCYCLIZATION
OLEFINS
PRIMARY AZIDES
TERMINAL ALKENES
HYDROAZIDATION
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Summary:A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00442f