Direct Pd-Catalyzed β-C(sp<sup>3</sup>)–H Hydroxylation of Aliphatic Carboxylic Acids

β-Hydroxy carbonyl scaffolds are of paramount importance due to their presence in a variety of natural products and bioactive molecules. In this study, we present a direct palladium-catalyzed β-C(sp<sup>3</sup>)-H hydroxylation of aliphatic carboxylic acids. The reported method employs convenient and readily available TBHP as an oxidant and provides an efficient, one-step route to a diverse range of β-hydroxy acids. Key aspects include the compatibility of this method with challenging α-non-quaternary carboxylic acids as substrates and excellent functional group tolerance. This newly developed method is expected to prove useful for generating compound libraries relevant to multiple disciplines.

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Publication Details

Journal
Organic Letters
Published
2025-06-11
DOI
https://doi.org/10.1021/acs.orglett.5c00614
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
3.74

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article

Direct Pd-Catalyzed β-C(sp3)–H Hydroxylation of Aliphatic Carboxylic Acids

Sourjya Mal, Manuel van Gemmeren, Tianxiao Xu
4 citations
Organic Letters
Catalytic C–H Functionalization Methods
3.74
article

Direct Pd-Catalyzed β-C(sp3)–H Hydroxylation of Aliphatic Carboxylic Acids

Sourjya Mal, Manuel van Gemmeren, Tianxiao Xu
article en
4 citations

Abstract

β-Hydroxy carbonyl scaffolds are of paramount importance due to their presence in a variety of natural products and bioactive molecules. In this study, we present a direct palladium-catalyzed β-C(sp<sup>3</sup>)-H hydroxylation of aliphatic carboxylic acids. The reported method employs convenient and readily available TBHP as an oxidant and provides an efficient, one-step route to a diverse range of β-hydroxy acids. Key aspects include the compatibility of this method with challenging α-non-quaternary carboxylic acids as substrates and excellent functional group tolerance. This newly developed method is expected to prove useful for generating compound libraries relevant to multiple disciplines.

Organic LettersVol. 27(25)
Christian-Albrechts-Universität zu Kiel (DE)
Deutsche Forschungsgemeinschaft, Christian-Albrechts-Universität zu Kiel
Openalex Percentile: Top 7%
Catalytic C–H Functionalization Methods
3.74
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Direct Pd-Catalyzed β-C(sp<sup>3</sup>)–H Hydroxylation of Aliphatic Carboxylic Acids — Sourjya Mal, Manuel van Gemmeren, et al. · Organic Letters (2025) | TGRS Research Map | TGRS