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

Jian Luo; Jian Zhang

doi:10.1021/acs.joc.6b01704

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

Jian Luo, Jian Zhang

Research output: Contribution to journal › Article › peer-review

56 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 language	English (US)
Pages (from-to)	9131-9137
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.6b01704
State	Published - Oct 7 2016

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.6b01704

Cite this

@article{ea889caea5474002983a7ccf3b436a6e,

title = "Aerobic Oxidation of Olefins and Lignin Model Compounds Using Photogenerated Phthalimide-N-oxyl Radical",

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.",

author = "Jian Luo and Jian Zhang",

note = "Funding Information: The authors are grateful for the support from the University of Nebraska-Lincoln. J.Z. is also grateful for the Donors of the American Chemical Society Petroleum Research Fund (53678-DNI10) and a National Science Foundation CAREER Award (DMR-1554918) for partial support of this research. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = oct,

day = "7",

doi = "10.1021/acs.joc.6b01704",

language = "English (US)",

volume = "81",

pages = "9131--9137",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Aerobic Oxidation of Olefins and Lignin Model Compounds Using Photogenerated Phthalimide-N-oxyl Radical

AU - Luo, Jian

AU - Zhang, Jian

N1 - Funding Information: The authors are grateful for the support from the University of Nebraska-Lincoln. J.Z. is also grateful for the Donors of the American Chemical Society Petroleum Research Fund (53678-DNI10) and a National Science Foundation CAREER Award (DMR-1554918) for partial support of this research. Publisher Copyright: © 2016 American Chemical Society.

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.

UR - http://www.scopus.com/inward/record.url?scp=84991010761&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84991010761&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b01704

DO - 10.1021/acs.joc.6b01704

M3 - Article

C2 - 27611186

AN - SCOPUS:84991010761

SN - 0022-3263

VL - 81

SP - 9131

EP - 9137

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this