One-Step Electrocatalytic Approach Applied to the Synthesis of β-Propiolactones from CO 2 and Dienes

β-Lactones are common substructures in a variety of natural products and drugs, and they serve as versatile synthetic intermediates in the production of valuable chemical derivatives. Traditional β-lactone synthesis relies on laborious multi-step synthetic methods that use toxic compounds, sophistic...

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Veröffentlicht in:Journal of organic chemistry 2023-08, Vol.88 (15), p.10403-10411
Hauptverfasser: Schwiedernoch, Renate, Niu, Xiaofeng, Shu, Haosheng, Steinmann, Stephan N, Wu, Mengjia, Naghavi, Negar
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Sprache:eng
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Zusammenfassung:β-Lactones are common substructures in a variety of natural products and drugs, and they serve as versatile synthetic intermediates in the production of valuable chemical derivatives. Traditional β-lactone synthesis relies on laborious multi-step synthetic methods that use toxic compounds, sophisticated catalysts, expensive, and/or reactive chemicals. Based on the in situ electrochemical formation of metal-based nanoclusters, this paper describes the development of a one-step, room temperature electrocatalytic method for the formation of stable β-lactone from CO and dienes. This one-step "electrosynthesis" method results in the formation of a new class of β-lactone with high selectivity (up to 100%) and activity (up to 80% yields with respect to the reacted diene) by regulating the applied potential and current density. This work paves the way for more sustainable and environmentally friendly reaction pathways based on the in situ formation of nanoclusters as organic electrosynthesis catalysts.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02441