Photoirradiation-Promoted <i>ipso</i> -Azidation of 1-Aryltriazenes
Ultraviolet (UV) irradiation (λ<sub>max</sub> = 370 nm) of a methanol solution of 1-aryltriazenes and azidotrimethylsilane promotes <i>ipso</i>-azidation. Optimization of the reaction conditions and a mechanistic study revealed that the hydrazoic acid generated in situ enabled efficient transformation. The high functional group tolerance of this reaction allowed for the transformation of a broad range of 1-aryltriazenes, including those introduced on a protein, to the corresponding aryl azides.
Authors
- Isao Kii (ORCID: https://orcid.org/0000-0002-6153-6250)
- Takamitsu Hosoya (ORCID: https://orcid.org/0000-0002-7270-351X)
- Takashi Niwa (ORCID: https://orcid.org/0000-0002-6209-5362)
- Kenji Watanabe (ORCID: https://orcid.org/0000-0001-6249-8666)
- Satoshi Fukuda
- Yamato Ezo
Institutions
- Kyushu University (JP)
- Shinshu University (JP)
- RIKEN Center for Biosystems Dynamics Research (JP)
- Doshisha Women's College of Liberal Arts (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-29
- DOI
- https://doi.org/10.1021/acs.orglett.5c03938
- Primary Topic
- Skin Protection and Aging
- Type
- article
- Field-Weighted Citation Impact
- 0.00