Direct Azidation of Phenols

Kitamura, Masaya; Murakami, Kento; Koga, Tatsuya; Eto, Takashi; Ishikawa, Akihiro; Shimooka, Hirokazu; Okauchi, Tatsuo

doi:10.1002/ejoc.201900967

Cited by 4 publications

(2 citation statements)

References 42 publications

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“…Recently, we developed direct azidation of phenols as shown in Scheme 1, eq. 2 [11] . In this reaction, use of excess amount of sodium azide and 2‐methoxyethanol as solvent was important.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Diazoquinones and Azidophenols via Diazo‐Transfer Reaction of Phenols

et al. 2022

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Dedicated to Professor Koichi Narasaka with Gratitude on the occasion of his 77th Birthday (Kiju).The first efficient diazo-transfer reaction of phenols is described. o-Quinone diazides (diazoquinones) were prepared from phenols in high yields by the diazo-transfer reaction using 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP, 2-PF 6 ), which is a safe and stable crystalline. The reaction efficiently proceeded in methanol in the presence of a base. Phenols substituted with electron-donating groups reacted more smoothly than those having electron withdrawing groups. Reactive phenols were diazotized by IPrAP with i Pr 2 NH as a base, and low reactive phenols were diazotized with N,Ndimethyl-4-aminopyridine (DMAP). Furthermore, the formed diazoquinones reacted with sodium azide in 2-methoxyethanol and afforded the corresponding azidophenol in high yields.

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Section: Introductionmentioning

confidence: 99%

“…2. [11] In this reaction, use of excess amount of sodium azide and 2-methoxyethanol as solvent was important. In our hypothesis, azidophenol was supposed to be synthesized by the reaction of phenol and azidoimidazolium 2 formed from 1 and sodium azide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diazoquinones and Azidophenols via Diazo‐Transfer Reaction of Phenols

et al. 2022

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Pd‐Catalyzed Intermolecular Transthiolation of Ar‐OTf Using Methyl 3‐(Methylthio) Propanoate as a Thiol Surrogate

Pan

Tian

et al. 2021

Eur J Org Chem

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A method for the odorless synthesis of unsymmetrical sulfides via Csp 2 À O and Csp 3 À S bond activation is presented. Using methyl 3-(methylthio) propanoate as a MeSH surrogate, a series of substituted aryl methyl sulfides have been obtained in moderate to good yields. This catalytic protocol can also tolerate methyl 3-(methylthio)propionate derivatives to afford the corresponding aryl sulfides.

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Five-membered ring systems: with more than one N atom

Yet

2021

Progress in Heterocyclic Chemistry

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Direct Azidation of Phenols

Abstract: Direct azidation of phenols was developed. By treating chloroimidazolinium chloride 1b and sodium azide with phenol in the presence of a secondary amine in methoxyethanol, ortho‐azidation of phenol was achieved.

Cited by 4 publications

References 42 publications

Synthesis of Diazoquinones and Azidophenols via Diazo‐Transfer Reaction of Phenols

Synthesis of Diazoquinones and Azidophenols via Diazo‐Transfer Reaction of Phenols

Pd‐Catalyzed Intermolecular Transthiolation of Ar‐OTf Using Methyl 3‐(Methylthio) Propanoate as a Thiol Surrogate

Five-membered ring systems: with more than one N atom

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