Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination

A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secon...

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Published inOrganic letters Vol. 23; no. 2; pp. 433 - 437
Main Authors Basnet, Prakash, Hong, Gang, Hendrick, Charles E., Kozlowski, Marisa C.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.01.2021
Subjects
alkenes
Alkenes - chemistry
carbon
Catalysis
Chemistry
Chemistry, Organic
chlorides
Copper
Halogenation
Lactones - chemistry
Molecular Structure
Nitriles - chemistry
oxidation
Oxidation-Reduction
Physical Sciences
Science & Technology
CHEMOSELECTIVE ACTIVATION
LACTONES
SP
C-H BONDS
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Summary:A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important gamma-lactones in one further step.
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SourceType-Scholarly Journals-1
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content type line 23
The manuscript was written through contributions of all authors. / All authors have given approval to the final version of the manuscript.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c03941