Phenoxysulfonyl azide: a new diazo-transfer reagent for the metal-free conversion of amines to azides

Sungduk Gwak; Ji Hye Lee; You Jeong You; Hyeok Jun Kwon; Hogyu Han

doi:10.1039/d5ob01124h

Phenoxysulfonyl azide: a new diazo-transfer reagent for the metal-free conversion of amines to azides

Sungduk Gwak^*
, Ji Hye Lee
, You Jeong You
, Hyeok Jun Kwon^*
, Hogyu Han^*

^*Corresponding author for this work

College of Science

Research output: Contribution to journal › Article › peer-review

Abstract

Phenoxysulfonyl azide (PSA, 1) was synthesized from 1,1′-sulfonylbis(2-methyl-1H-imidazole) (2) and studied for its diazo-transfer reactivity. The reaction with 1 was found to convert primary amines 3 into their corresponding azides 4, even without a metal catalyst. Accordingly, PSA is a new diazo-transfer reagent for the metal-free conversion of amines to azides, thereby facilitating the preparation of organic azides from biomolecules.

Original language	English
Pages (from-to)	10974-10978
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	23
Issue number	48
DOIs	https://doi.org/10.1039/d5ob01124h
Publication status	Published - 2025 Dec 28

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Publisher Copyright:
This journal is © The Royal Society of Chemistry, 2025

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d5ob01124h

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title = "Phenoxysulfonyl azide: a new diazo-transfer reagent for the metal-free conversion of amines to azides",

abstract = "Phenoxysulfonyl azide (PSA, 1) was synthesized from 1,1′-sulfonylbis(2-methyl-1H-imidazole) (2) and studied for its diazo-transfer reactivity. The reaction with 1 was found to convert primary amines 3 into their corresponding azides 4, even without a metal catalyst. Accordingly, PSA is a new diazo-transfer reagent for the metal-free conversion of amines to azides, thereby facilitating the preparation of organic azides from biomolecules.",

author = "Sungduk Gwak and Lee, \{Ji Hye\} and You, \{You Jeong\} and Kwon, \{Hyeok Jun\} and Hogyu Han",

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T1 - Phenoxysulfonyl azide

T2 - a new diazo-transfer reagent for the metal-free conversion of amines to azides

AU - Gwak, Sungduk

AU - Lee, Ji Hye

AU - You, You Jeong

AU - Kwon, Hyeok Jun

AU - Han, Hogyu

PY - 2025/12/28

Y1 - 2025/12/28

N2 - Phenoxysulfonyl azide (PSA, 1) was synthesized from 1,1′-sulfonylbis(2-methyl-1H-imidazole) (2) and studied for its diazo-transfer reactivity. The reaction with 1 was found to convert primary amines 3 into their corresponding azides 4, even without a metal catalyst. Accordingly, PSA is a new diazo-transfer reagent for the metal-free conversion of amines to azides, thereby facilitating the preparation of organic azides from biomolecules.

AB - Phenoxysulfonyl azide (PSA, 1) was synthesized from 1,1′-sulfonylbis(2-methyl-1H-imidazole) (2) and studied for its diazo-transfer reactivity. The reaction with 1 was found to convert primary amines 3 into their corresponding azides 4, even without a metal catalyst. Accordingly, PSA is a new diazo-transfer reagent for the metal-free conversion of amines to azides, thereby facilitating the preparation of organic azides from biomolecules.

UR - https://www.scopus.com/pages/publications/105023194113

U2 - 10.1039/d5ob01124h

DO - 10.1039/d5ob01124h

M3 - Article

C2 - 41312573

AN - SCOPUS:105023194113

SN - 1477-0520

VL - 23

SP - 10974

EP - 10978

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 48

ER -

Phenoxysulfonyl azide: a new diazo-transfer reagent for the metal-free conversion of amines to azides

Abstract

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