4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 21, Pages 3340-3343

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00442f

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Funding

  1. National Natural Science Foundation of China [20932002, 21172076]
  2. National Basic Research Program of China (973 Program) [2011CB808600]
  3. Changjiang Scholars and Innovation Team Project of the Ministry of Education

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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.

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