Oxidative Cleavage of β-Substituted Primary Alcohols in Flow

Herein, we report a scalable oxidative cleavage of β-substituted primary alcohols under continuous-flow conditions using a silica-supported hypervalent iodine(V) catalyst and TBA-Oxone as terminal oxidant. The method enables rapid and selective synthesis of γ-lactones and γ-lactams under mild conditions with broad substrate scope and high functional group tolerance. The catalyst is reusable for >15 cycles, and the process is readily scalable. Moreover, this technology offers a readily scalable and sustainable process for the synthesis of γ-butyrolactone from tetrahydrofurfuryl alcohol.

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Publication Details

Journal
Organic Letters
Published
2026-01-06
DOI
https://doi.org/10.1021/acs.orglett.5c04782
Citations
1
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
22.95
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Oxidative Cleavage of β-Substituted Primary Alcohols in Flow

Michael Tapera, Athanasios Savvidis, Cedric Meysing, Stefan F. Kirsch et al.
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Oxidative Organic Chemistry Reactions
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article

Oxidative Cleavage of β-Substituted Primary Alcohols in Flow

Michael Tapera, Athanasios Savvidis, Cedric Meysing, Stefan F. Kirsch, Adrián Gómez-Suárez
article en
1 citations

Abstract

Herein, we report a scalable oxidative cleavage of β-substituted primary alcohols under continuous-flow conditions using a silica-supported hypervalent iodine(V) catalyst and TBA-Oxone as terminal oxidant. The method enables rapid and selective synthesis of γ-lactones and γ-lactams under mild conditions with broad substrate scope and high functional group tolerance. The catalyst is reusable for >15 cycles, and the process is readily scalable. Moreover, this technology offers a readily scalable and sustainable process for the synthesis of γ-butyrolactone from tetrahydrofurfuryl alcohol.

Organic LettersVol. 28(2)
University of Wuppertal (DE)
Responsible consumption and production
Openalex Percentile: Top 3%
Oxidative Organic Chemistry Reactions
22.95
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