Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes

Ultraviolet (UV) irradiation (λ_<max> = 370 nm) of a methanol solution of 1-aryltriazenes and azidotrimethylsilane promotes ipso-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.

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Publication Details

Journal
QIR (Kyushu University Institutional Repository) (Kyushu University)
Published
2025-09-29
Primary Topic
Chemical Reactions and Mechanisms
Type
article
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article

Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes

Isao Kii, Takamitsu Hosoya, Takashi Niwa, Satoshi Fukuda et al.
QIR (Kyushu University Institutional Repository) (Kyushu University)
Chemical Reactions and Mechanisms
article

Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes

Isao Kii, Takamitsu Hosoya, Takashi Niwa, Satoshi Fukuda, Yamato Ezo
article en

Abstract

Ultraviolet (UV) irradiation (λ_<max> = 370 nm) of a methanol solution of 1-aryltriazenes and azidotrimethylsilane promotes ipso-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.

QIR (Kyushu University Institutional Repository) (Kyushu University)
Openalex Percentile: Top 22%
Chemical Reactions and Mechanisms
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Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes — Isao Kii, Takamitsu Hosoya, et al. · QIR (Kyushu University Institutional Repository) (Kyushu University) (2025) | TGRS Research Map | TGRS