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Economical, green, and safe route towards substituted lactones by anodic generation of oxycarbonyl radicals

Economical, green, and safe route towards substituted lactones by anodic generation of oxycarbonyl radicals

Petti, Alessia, Leech, Matthew C., Garcia, Anthony D., Goodall, Iain C.A., Dobbs, Adrian P. ORCID: 0000-0002-7241-7118 and Lam, Kevin ORCID: 0000-0003-1481-9212 (2019) Economical, green, and safe route towards substituted lactones by anodic generation of oxycarbonyl radicals. Angewandte Chemie International Edition, 58 (45). pp. 16115-16118. ISSN 1433-7851 (Print), 1521-3773 (Online) (doi:https://doi.org/10.1002/anie.201909922)

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Abstract

A new electrochemical methodology has been developed for the generation of oxycarbonyl radicals under mild and green conditions from readily available hemioxalate salts. Mono‐ and multi‐functionalised γ‐butyrolactones were synthesised through exo‐cyclisation of these oxycarbonyl radicals with an alkene, followed by the sp3–sp3 capture of the newly formed carbon‐centred radical. The synthesis of functionalised valerolactone derivatives was also achieved, demonstrating the versatility of the newly developed methodology. This represents a viable synthetic route towards pharmaceutically important fragments and further demonstrates the practicality of electrosynthesis as a green and economical method to activate small organic molecules.

Item Type: Article
Uncontrolled Keywords: electrosynthesis, radicals, oxycarbonyl, electrochemistry, organic chemistry
Subjects: T Technology > TA Engineering (General). Civil engineering (General)
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 21 Oct 2020 22:31
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: REF 1
URI: http://gala.gre.ac.uk/id/eprint/25297

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