TY - JOUR
T1 - Aerobic Oxidation of Olefins and Lignin Model Compounds Using Photogenerated Phthalimide-N-oxyl Radical
AU - Luo, Jian
AU - Zhang, Jian
PY - 2016/10/7
Y1 - 2016/10/7
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.6b01704
DO - 10.1021/acs.joc.6b01704
M3 - Article
C2 - 27611186
AN - SCOPUS:84991010761
VL - 81
SP - 9131
EP - 9137
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -