Rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids under sunlight: DFT mechanistic studies

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TitreRongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids under sunlight: DFT mechanistic studies
Type de publicationJournal Article
Year of Publication2020
AuteursGolla S, Poshala S, Pawar R, Kokatla HPrasad
JournalTETRAHEDRON LETTERS
Volume61
Pagination151539
Date PublishedFEB 27
Type of ArticleArticle
ISSN0040-4039
Mots-clésAerobic oxidation, Arylboronic acid, Rongalite, Superoxide radical anion
Résumé

A novel rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids has been developed. This method employs low-cost rongalite as a radical initiator and O-2 as a green oxidizing agent for ipso-hydroxylation. This protocol is compatible with a wide variety of functional groups with good to excellent yields at room temperature. Furthermore, mechanistic insight into the role of superoxide radical anions in C-B cleavage has also been provided based on DFT studies. (C) 2019 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2019.151539