Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions

A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-10, Vol.12 (38), p.7489-7493
Main Authors: Yoshida, Suguru, Nonaka, Takako, Morita, Takamoto, Hosoya, Takamitsu
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Benzene - chemistry
Cycloaddition Reaction
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl triflates bearing a base-sensitive terminal alkyne moiety, which was achieved using trimethylsilylmethyl Grignard reagent.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01654h