Iron-Catalyzed Reductive Ring-Rearrangement Reaction of Bridged Benzo[<i>b</i>]oxocin-4-ones with Grignard Reagents to Afford Bridged Benzo[<i>b</i>]oxocin-2-ols

An iron-catalyzed reductive ring-rearrangement reaction of bridged benzo[<i>b</i>]oxocin-4-ones with Grignard reagents to produce bridged benzo[<i>b</i>]oxocin-2-ols is reported. Mechanistic studies indicate that an iron redox catalysis cycle involving oxidative addition to the C-O bond by low-valence iron and β-methoxyl elimination as key steps operates in this reaction.

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Publication Details

Journal
Organic Letters
Published
2025-03-11
DOI
https://doi.org/10.1021/acs.orglett.5c00451
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.87

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article

Iron-Catalyzed Reductive Ring-Rearrangement Reaction of Bridged Benzo[b]oxocin-4-ones with Grignard Reagents to Afford Bridged Benzo[b]oxocin-2-ols

Dunru Zhu, Ruwei Shen, Yishuai Fan, Run-Jie Peng et al.
2 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.87
article

Iron-Catalyzed Reductive Ring-Rearrangement Reaction of Bridged Benzo[b]oxocin-4-ones with Grignard Reagents to Afford Bridged Benzo[b]oxocin-2-ols

Dunru Zhu, Ruwei Shen, Yishuai Fan, Run-Jie Peng, Haoran Yang
article en
2 citations

Abstract

An iron-catalyzed reductive ring-rearrangement reaction of bridged benzo[<i>b</i>]oxocin-4-ones with Grignard reagents to produce bridged benzo[<i>b</i>]oxocin-2-ols is reported. Mechanistic studies indicate that an iron redox catalysis cycle involving oxidative addition to the C-O bond by low-valence iron and β-methoxyl elimination as key steps operates in this reaction.

Organic LettersVol. 27(11)
Nanjing Tech University (CN), State Key Laboratory of Materials-Oriented Chemical Engineering
National Natural Science Foundation of China, Nanjing Tech University, State Key Laboratory of Materials- Oriented Chemical Engineering, Graduate Research and Innovation Projects of Jiangsu Province
Openalex Percentile: Top 17%
Catalytic C–H Functionalization Methods
1.87
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