Gold-Mediated Cyclization of <i>N</i>-Acrylamides via Energy Transfer Photocatalysis

We disclose a gold-mediated photocyclization method for the efficient synthesis of acrylamide-derived β-lactams and 3,4-dihydroquinolin-2-ones, two privileged bioactive scaffolds. The protocol proceeds with ease, providing good yields of product while exhibiting excellent functional group tolerance at low catalyst loadings in sustainable solvents. Additionally, reaction times are significantly reduced compared with prior-art methods. Notably, the present gold system exhibits superior performance in activating poorly conjugated substrates, which are typically unreactive with other photocatalysts, highlighting the exceptional position of this organogold system among modern photocatalysts.

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Publication Details

Journal
Organic Letters
Published
2024-11-26
DOI
https://doi.org/10.1021/acs.orglett.4c03919
Citations
8
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.00

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article

Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis

Sébastien G. Guillet, Vladislav A. Voloshkin, Steven P. Nolan, Yuan Zhao
8 citations
Organic Letters
Radical Photochemical Reactions
2.00
article

Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis

Sébastien G. Guillet, Vladislav A. Voloshkin, Steven P. Nolan, Yuan Zhao
article en
8 citations

Abstract

We disclose a gold-mediated photocyclization method for the efficient synthesis of acrylamide-derived β-lactams and 3,4-dihydroquinolin-2-ones, two privileged bioactive scaffolds. The protocol proceeds with ease, providing good yields of product while exhibiting excellent functional group tolerance at low catalyst loadings in sustainable solvents. Additionally, reaction times are significantly reduced compared with prior-art methods. Notably, the present gold system exhibits superior performance in activating poorly conjugated substrates, which are typically unreactive with other photocatalysts, highlighting the exceptional position of this organogold system among modern photocatalysts.

Organic LettersVol. 26(48)
Ghent University (BE)
Fonds Wetenschappelijk Onderzoek, China Scholarship Council, Bijzonder Onderzoeksfonds UGent
Affordable and clean energy
Openalex Percentile: Top 14%
Radical Photochemical Reactions
2.00
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Gold-Mediated Cyclization of <i>N</i>-Acrylamides via Energy Transfer Photocatalysis — Sébastien G. Guillet, Vladislav A. Voloshkin, et al. · Organic Letters (2024) | TGRS Research Map | TGRS