ChemComm
Communication
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Scheme 2 Control experiments.
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Scheme 3 Proposed mechanism.
to produce the intermediate 5.10a,c,11,12,14 Subsequently, 5
attacks the imine 6, which is generated by the oxidation of
2a, to provide the intermediate 7. 7 equilibrates to intermediate
8 under optimized conditions. Compound 9, which is generated
by the oxidation of 8, leads to compound 10 via intramolecular
cyclization. Finally, the product 3aa is achieved by elimination of
the primary amine of 10.
In summary, we have developed a novel and efficient
method to synthesise substituted imidazoles from vinyl azides
and benzylamines under the I2/TBHP catalytic reaction system.
Various substituents of vinyl azides and benzylamines are
tolerated well in this approach resulting in the desired products
in moderate to good yields.
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Notes and references
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