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Updated: May 11, 2025
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Boronate Formation-Triggered Azide-Alkyne Cycloaddition
Jumpei Taguchi1, Yohei Ohata1, Honoka Akimoto1
1Chemical Bioscience Team, Laboratory for Biomaterials and Bioengineering, Institute of Integrated Research, Institute of Science Tokyo, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
Abstract:
A catalyst-free triazole formation reaction between o-borylaryl azides and N-propargyldiethanolamine derivatives is reported. Control experiments demonstrated that the triazole formation was triggered by boronate formation, which brought the azido group and alkyne moiety into close proximity. This boronate formation-triggered azide-alkyne cycloaddition (BAAC) reaction exhibited orthogonality to other azide-alkyne cycloaddition reactions, enabling sequential double-click conjugations with diazido or dialkyne compounds.
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