Synthesis of Diazoquinones and Azidophenols via Diazo‐Transfer Reaction of Phenols
- 12 May 2022
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2022 (18)
Abstract
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‐PF6), 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 iPr2NH as a base, and low reactive phenols were diazotized with N,N‐dimethyl‐4‐aminopyridine (DMAP). Furthermore, the formed diazoquinones reacted with sodium azide in 2‐methoxyethanol and afforded the corresponding azidophenol in high yields.Keywords
Funding Information
- Japan Society for the Promotion of Science (20H02744, 21 K18964)
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