Highly Efficient CH Hydroxylation of Carbonyl Compounds with Oxygen under Mild Conditions

A transition‐metal‐free Cs2CO3‐catalyzed α‐hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α‐hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industr...

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Published inAngewandte Chemie International Edition Vol. 53; no. 2; pp. 548 - 552
Main Authors Liang, Yu-Feng, Jiao, Ning
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 07.01.2014
WILEY‐VCH Verlag
Wiley
Subjects
Bonding
Carbamates - chemical synthesis
Carbamates - chemistry
Carbonyl compounds
Catalysis
cesium
Chemistry
Chemistry, Multidisciplinary
Cleavage
CH functionalization
dioxygen
Hydrogen Bonding
Hydroxylation
Molecular Structure
Oxidants
Oxidizing agents
Oxygen - chemistry
oxygenation
Pharmaceuticals
Physical Sciences
Science & Technology
Transformations
cesium
dioxygen
ORGANIC-CHEMICALS
hydroxylation
1,3-DICARBONYL COMPOUNDS
BOND FORMATION
oxygenation
KETONES
AEROBIC OXYGENATION
ELECTRON-TRANSFER
CH functionalization
ALPHA-HYDROXYLATION
PALLADIUM-CATALYZED OXIDATION
SINGLET OXYGEN
MOLECULAR-OXYGEN
CH functionalization
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Summary:A transition‐metal‐free Cs2CO3‐catalyzed α‐hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α‐hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)H bond cleavage. OH, so simple! A transition‐metal‐free Cs2CO3‐catalyzed α‐hydroxylation of carbonyl compounds with O2 provided a variety of tertiary α‐hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.
Bibliography:Financial support from the National Basic Research Program of China (973 Program; Grant No. 2009CB825300), the National Science Foundation of China (No. 21172006), and the National Young Top-Notch Talent Support Program are greatly appreciated. We thank Xiaoyang Wang of this research group for reproducing the results for 2 h and 2 i.
National Science Foundation of China - No. 21172006
National Basic Research Program of China - No. 2009CB825300
ark:/67375/WNG-JL90M903-N
istex:EF65569954F705098ABC5849CF173218FB4AEE3F
ArticleID:ANIE201308698
2 h
Financial support from the National Basic Research Program of China (973 Program; Grant No. 2009CB825300), the National Science Foundation of China (No. 21172006), and the National Young Top‐Notch Talent Support Program are greatly appreciated. We thank Xiaoyang Wang of this research group for reproducing the results for
and
2 i
.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201308698