Copper-catalyzed oxidative coupling of quinoxalin-2(1H)-ones with alcohols: access to hydroxyalkylation of quinoxalin-2(1H)-ones

An efficient copper-catalyzed protocol for the synthesis of hydroxyl-containing quinoxalin-2(1H)-ones from the radical reaction of quinoxalin-2(1H)-ones with alcohols was developed with moderate to good yields. Quinoxalin-2(1H)-ones were coupled with alkyl radicals through direct catalytic functiona...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 23; pp. 3382 - 3390
Main Authors Fu, Junhao, Yuan, Jinwei, Zhang, Yue, Xiao, Yongmei, Mao, Pu, Diao, Xiaoqiong, Qu, Lingbo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.12.2018
Royal Society of Chemistry
Subjects
Alcohol
Alcohols
Atom economy
Catalysis
Chemical synthesis
Chemistry
Chemistry, Organic
Copper
Functional groups
Hydrogen bonds
Organic chemistry
Physical Sciences
Science & Technology
Substrates
OXYGEN
ETHERS
DIRECT FUNCTIONALIZATION
C-C BOND
ARYLATION
H BONDS
NUCLEOPHILIC-ADDITION
N-OXIDES
ADJACENT
GRIGNARD-REAGENTS
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Summary:An efficient copper-catalyzed protocol for the synthesis of hydroxyl-containing quinoxalin-2(1H)-ones from the radical reaction of quinoxalin-2(1H)-ones with alcohols was developed with moderate to good yields. Quinoxalin-2(1H)-ones were coupled with alkyl radicals through direct catalytic functionalization of the sp(3) C-H bond of alcohols. The methodology demonstrates a broad substrate scope, excellent functional group tolerance, high atom economy and high efficiency, thus enabling the preparation of diverse potentially valuable hydroxyl-containing quinoxalin-2(1H)-ones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c8qo00979a