Flavin-Catalyzed Chemoselective Aerobic Oxygenation of Heteroarylmethanes to Ketones

A novel flavin-catalyzed chemoselective aerobic oxygenation of arylheteroarylmethanes to ketones has been developed under metal-free and mild conditions. This catalytic system employs a cationic flavin to activate sp<sup>3</sup> C-H bonds through the formation of pyridinium-flavin adducts, enabling precise proton and electron transfer for oxygen atom insertion. As a result, this method exhibits high chemoselectivity, effectively distinguishing between arylheteroarylmethanes and diarylmethanes.

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Publication Details

Journal
Organic Letters
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.orglett.5c00414
Citations
6
Primary Topic
Chemical Reactions and Isotopes
Type
article
Field-Weighted Citation Impact
4.74

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article

Flavin-Catalyzed Chemoselective Aerobic Oxygenation of Heteroarylmethanes to Ketones

Hiroki Iida, Tatsuki Fukuda, Hazuki Miyake
6 citations
Organic Letters
Chemical Reactions and Isotopes
4.74
article

Flavin-Catalyzed Chemoselective Aerobic Oxygenation of Heteroarylmethanes to Ketones

Hiroki Iida, Tatsuki Fukuda, Hazuki Miyake
article en
6 citations

Abstract

A novel flavin-catalyzed chemoselective aerobic oxygenation of arylheteroarylmethanes to ketones has been developed under metal-free and mild conditions. This catalytic system employs a cationic flavin to activate sp<sup>3</sup> C-H bonds through the formation of pyridinium-flavin adducts, enabling precise proton and electron transfer for oxygen atom insertion. As a result, this method exhibits high chemoselectivity, effectively distinguishing between arylheteroarylmethanes and diarylmethanes.

Organic LettersVol. 27(12)
Shimane University (JP)
Shimane University, Electric Technology Research Foundation of Chugoku, Japan Society for the Promotion of Science, Japan Science and Technology Agency
Openalex Percentile: Top 6%
Chemical Reactions and Isotopes
4.74
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