Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis

A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The gener...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 83; pp. 1253 - 12533
Main Authors Zhang, Hong, Xiao, Qian, Qi, Xu-Kuan, Gao, Xue-Wang, Tong, Qing-Xiao, Zhong, Jian-Ji
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 20.10.2020
Royal Society of Chemistry
Subjects
Alkenes
Carbonyl compounds
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Decarboxylation
Dehydrogenation
Ketones
Physical Sciences
Science & Technology
Substrates
FUNCTIONALIZATION
HYDROGEN
ACIDS
CHEMISTRY
RADICAL REACTIONS
HIGHLY EFFICIENT
WATER
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Summary:A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins. The selective synthesis of allylic ketones and 1,4-dicarbonyl compounds by photoredox/cobaloxime co-catalysis and photoredox catalysis, respectively, is described herein.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/d0cc05580h
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05580h