HBr–H <sub>2</sub> O <sub>2</sub> –Promoted Achmatowicz Rearrangement

The Achmatowicz rearrangement enables the oxidative ring expansion of furfuryl alcohols into dihydropyranones, key motifs in natural products. Herein, we report a mild, metal-free method using a HBr-H<sub>2</sub>O<sub>2</sub> system as an inexpensive source of electrophilic bromine species. The optimized conditions accommodate a broad range of primary, secondary, and tertiary furfuryl alcohols, providing a practical approach to access structurally diverse pyranone scaffolds.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-05
DOI
https://doi.org/10.1021/acs.joc.5c02820
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00
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article

HBr–H 2 O 2 –Promoted Achmatowicz Rearrangement

Jiang‐Fei Li, Ting Sun, Qin Zhu, Wenchao Zhu et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

HBr–H 2 O 2 –Promoted Achmatowicz Rearrangement

Jiang‐Fei Li, Ting Sun, Qin Zhu, Wenchao Zhu, Shaoyin Wang
article en

Abstract

The Achmatowicz rearrangement enables the oxidative ring expansion of furfuryl alcohols into dihydropyranones, key motifs in natural products. Herein, we report a mild, metal-free method using a HBr-H<sub>2</sub>O<sub>2</sub> system as an inexpensive source of electrophilic bromine species. The optimized conditions accommodate a broad range of primary, secondary, and tertiary furfuryl alcohols, providing a practical approach to access structurally diverse pyranone scaffolds.

The Journal of Organic ChemistryVol. 91(7)
Wannan Medical College (CN)
Openalex Percentile: Top 64%
Catalytic C–H Functionalization Methods
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