A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates

Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation has been developed, which efficiently converts the traditionally challenging substrate class of protected allylic alcohols to the corresponding acyloin products. Additionally, the catalyt...

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Published inJournal of the American Chemical Society Vol. 131; no. 17; pp. 6076 - 6077
Main Authors Michel, Brian W, Camelio, Andrew M, Cornell, Candace N, Sigman, Matthew S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2009
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Physical Sciences
Science & Technology
tert-Butylhydroperoxide - chemistry
OLEFINS
METHYL KETONES
DISCOVERY
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Summary:Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation has been developed, which efficiently converts the traditionally challenging substrate class of protected allylic alcohols to the corresponding acyloin products. Additionally, the catalytic system is general for several other substrate classes, converting terminal olefins to methyl ketones, with short reaction times. The system is scalable (20 mmol) and can be performed with a reduced catalyst loading of 1 mol%. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja901212h