Metal-free iminyl radical-mediated C-C single bond cleavage/functionalization of redox-active oxime esters

A visible-light-driven iminyl radical-mediated C-C bond cleavage and functionalization of cycloketone oxime esters have been accomplished. This protocol is simple and does not require expensive and toxic photoredox and/or transition-metal catalysis, providing a novel catalyst-free strategy for alkyl...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 3; pp. 622 - 627
Main Authors Zhang, Miao-Miao, Li, Shi-Hong, Tu, Jia-Lin, Min, Qing-Qiang, Liu, Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.02.2020
Royal Society of Chemistry
Subjects
Alkylation
Allyl compounds
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry, Organic
Cleavage
Covalent bonds
Esters
NMR
Nuclear magnetic resonance
Organic chemistry
Oxime esters
Physical Sciences
Science & Technology
Transition metals
KETONES
CYANOFLUORINATION
HYDROGENATION
REDUCTION
NITRILES
CYCLOBUTANONE O-BENZOYLOXIMES
LIGHT
RING-CLEAVAGE
HANTZSCH ESTERS
VINYL ETHERS
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Summary:A visible-light-driven iminyl radical-mediated C-C bond cleavage and functionalization of cycloketone oxime esters have been accomplished. This protocol is simple and does not require expensive and toxic photoredox and/or transition-metal catalysis, providing a novel catalyst-free strategy for alkylation, allylation, vinylation and alkynylation through addition of C(sp(3))-centered radicals to various unsaturated acceptors. The commercially available and photoactive Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo01446b