CuI/TEMPO-mediated aerobic oxidative sp <sup>3</sup> C–H functionalization affording pyrrol-2-one derivatives

5-Hydroxy-1<i>H</i>-pyrrol-2-ones represent a very important class of compounds. However, their syntheses rely on precursors that are exotic and commercially unavailable, or on multistep operations. A cascade reaction can evade multistep syntheses, but most substrates are not amenable to cascade strategies. We thoughtfully designed a cascade strategy, choosing the Knoevenagel product of a ketone and malononitrile as a very trivial starting material. This strategy afforded 5-hydroxy-1<i>H</i>-pyrrol-2-ones <i>via</i> a cascade of C(sp<sup>3</sup>)-H functionalization, directed nitrile hydrolysis and C-N bond-forming reactions.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01297j
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

CuI/TEMPO-mediated aerobic oxidative sp 3 C–H functionalization affording pyrrol-2-one derivatives

Tanmoy Dutta, Saikat Khamarui, Bholanath Maity, Souvik Mondal et al.
Organic & Biomolecular Chemistry
Catalytic C–H Functionalization Methods
article

CuI/TEMPO-mediated aerobic oxidative sp 3 C–H functionalization affording pyrrol-2-one derivatives

Tanmoy Dutta, Saikat Khamarui, Bholanath Maity, Souvik Mondal, Abhijit Hazra, S.K. Mandal, Suman Ray, Aritra Mondal, Paramita Das
article en

Abstract

5-Hydroxy-1<i>H</i>-pyrrol-2-ones represent a very important class of compounds. However, their syntheses rely on precursors that are exotic and commercially unavailable, or on multistep operations. A cascade reaction can evade multistep syntheses, but most substrates are not amenable to cascade strategies. We thoughtfully designed a cascade strategy, choosing the Knoevenagel product of a ketone and malononitrile as a very trivial starting material. This strategy afforded 5-hydroxy-1<i>H</i>-pyrrol-2-ones <i>via</i> a cascade of C(sp<sup>3</sup>)-H functionalization, directed nitrile hydrolysis and C-N bond-forming reactions.

Organic & Biomolecular ChemistryVol. 23(47)
Jawaharlal Nehru Centre for Advanced Scientific Research (IN), Presidency University (IN), KPC Medical College and Hospital (IN), King Abdullah University of Science and Technology (SA), University of Kalyani (IN)
Openalex Percentile: Top 75%
Catalytic C–H Functionalization Methods
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CuI/TEMPO-mediated aerobic oxidative sp <sup>3</sup> C–H functionalization affording pyrrol-2-one derivatives — Tanmoy Dutta, Saikat Khamarui, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS