Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature

A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substit...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 17; pp. 5094 - 5097
Main Authors Lippincott, Daniel J, Trejo-Soto, Pedro J, Gallou, Fabrice, Lipshutz, Bruce H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
OXYGEN
ALKENES
C DOUBLE-BOND
MECHANISM
PEROXIDES
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Summary:A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01883