Boronate Formation-Triggered Azide–Alkyne Cycloaddition
A catalyst-free triazole formation reaction between <i>o</i>-borylaryl azides and <i>N</i>-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.
Authors
- Hitomi Tabuchi
- Yasuo Ohata
- Jumpei Taguchi (ORCID: https://orcid.org/0000-0003-2337-9132)
- Takamitsu Hosoya (ORCID: https://orcid.org/0000-0002-7270-351X)
- Katsuhiko Tomooka (ORCID: https://orcid.org/0000-0002-0762-5746)
- Takashi Niwa (ORCID: https://orcid.org/0000-0002-6209-5362)
- Kazunobu Igawa (ORCID: https://orcid.org/0000-0002-7354-5162)
- Hiroyuki Akimoto
Institutions
- Kyushu University (JP)
- RIKEN Center for Biosystems Dynamics Research (JP)
- Kumamoto University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-18
- DOI
- https://doi.org/10.1021/acs.orglett.5c00732
- Citations
- 1
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Japan Agency for Medical Research and Development
- Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science
- Core Research for Evolutional Science and Technology