Highly Atom-Efficient Oxidation of Electron-Deficient Internal Olefins to Ketones Using a Palladium Catalyst

A 100 % atom‐efficient synthesis of ketones from electron‐deficient internal olefins was achieved using O2 as a “green” oxidant (see scheme, DMA=N,N‐dimethylacetamide, EWG=electron‐withdrawing group). Various electron‐deficient olefins were oxidized to the corresponding ketones with over 99 % select...

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Published inAngewandte Chemie International Edition Vol. 52; no. 23; pp. 5961 - 5964
Main Authors Mitsudome, Takato, Yoshida, Syuhei, Mizugaki, Tomoo, Jitsukawa, Koichiro, Kaneda, Kiyotomi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.06.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Chemistry
Chemistry, Multidisciplinary
Formations
Isomers
Ketones
molecular oxygen
Olefins
Oxidants
oxidation
Palladium
Physical Sciences
Science & Technology
Selectivity
Synthesis
REGIOSELECTIVE OXIDATION
SYSTEM
oxidation
REOXIDANT
palladium
WACKER REACTION
ketones
molecular oxygen
olefins
MOLECULAR-OXYGEN
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Summary:A 100 % atom‐efficient synthesis of ketones from electron‐deficient internal olefins was achieved using O2 as a “green” oxidant (see scheme, DMA=N,N‐dimethylacetamide, EWG=electron‐withdrawing group). Various electron‐deficient olefins were oxidized to the corresponding ketones with over 99 % selectivity and without the formation of olefin isomers or their oxidized products.
Bibliography:JSPS KAKENHI - No. 23686116; No. 23360357; No. 24246129; No. 22360339
ark:/67375/WNG-M95D7V1B-V
ArticleID:ANIE201301611
This work was supported by JSPS KAKENHI (grant numbers 23686116, 23360357, 24246129, and 22360339).
istex:8E3A24FDC721C59829A510065D6CB364E3DC87BD
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201301611