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 language | English (US) |
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Pages (from-to) | 9131-9137 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 81 |
Issue number | 19 |
DOIs | |
State | Published - Oct 7 2016 |
ASJC Scopus subject areas
- Organic Chemistry