Azido-type-selective triazole formation by iridium-catalyzed cycloaddition with thioalkynes

The iridium-catalyzed azide-thioalkyne cycloaddition was found to proceed much faster with benzyl azide than with phenyl azide. The high azido-type selectivity was also observed in other combinations of azides with different steric environments. This finding enabled the efficient assembly of three a...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (42), p.6235-6238
Main Authors: Sugiyama, Kazuya, Sakata, Yuki, Niwa, Takashi, Yoshida, Suguru, Hosoya, Takamitsu
Format: Article
Language:English
Subjects:
Alkynes
Azide
Azides
Catalysis
Copper
Cycloaddition
Cycloaddition Reaction
Iridium
Selectivity
Triazoles
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Summary:The iridium-catalyzed azide-thioalkyne cycloaddition was found to proceed much faster with benzyl azide than with phenyl azide. The high azido-type selectivity was also observed in other combinations of azides with different steric environments. This finding enabled the efficient assembly of three azidophilic molecules to triazido platforms by three sequential triazole-forming reactions. Iridium-catalyzed azide-thioalkyne cycloaddition was found to be effective for the azido-type-selective reaction of various multiazido compounds, enabling facile synthesis of multitriazole compounds in short steps.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01739c