Aerobic Oxidation of Olefins and Lignin Model Compounds Using Photogenerated Phthalimide-N-oxyl Radical

Jian Luo, Jian Zhang

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

A metal-free protocol to generate phthalimide-N-oxyl (PINO) radicals from N-hydroxyphthalimide (NHPI) via a photoinduced proton-coupled electron transfer process is reported. Using donor-substituted aromatic ketones, such as 4,4′-bis(diphenylamino)benzophenone (DPA-BP), PINO radicals are efficiently produced and subsequently utilized to functionalize olefins to afford a new class of alkyl hydroperoxides. The DPA-BP/NHPI/O2 photocatalytic system exhibits high efficiency toward the aerobic oxidation of β-O-4 lignin models.

Original languageEnglish (US)
Pages (from-to)9131-9137
Number of pages7
JournalJournal of Organic Chemistry
Volume81
Issue number19
DOIs
Publication statusPublished - Oct 7 2016

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ASJC Scopus subject areas

  • Organic Chemistry

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