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Economical, Green, and Safe Route Towards Substituted Lactones by Anodic Generation of Oxycarbonyl Radicals
Author(s) -
Petti Alessia,
Leech Matthew C.,
Garcia Anthony D.,
Goodall Iain C. A.,
Dobbs Adrian P.,
Lam Kevin
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909922
Subject(s) - radical , electrosynthesis , alkene , chemistry , electrochemistry , combinatorial chemistry , molecule , organic chemistry , catalysis , electrode
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 sp 3 –sp 3 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.