Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbon‒oxygen bonds

Ni(0)/NHC-based catalyst system can promote the amination of N-heteroaryl methyl ethers via the cleavage of normally unreactive carbon–oxygen bonds. Electron-deficient N-heteroarenes including pyridine, quinoline, isoquinoline, and quinoxaline undergo amination to afford aminopyridine and related he...

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Bibliographic Details
Published inTetrahedron Vol. 68; no. 26; pp. 5157 - 5161
Main Authors Tobisu, Mamoru, Yasutome, Ayaka, Yamakawa, Ken, Shimasaki, Toshiaki, Chatani, Naoto
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.07.2012
Elsevier
Subjects
Amination
Catalysis
Chemistry
Chemistry, Organic
C–O bond activation
Heteroarene
Nickel
Physical Sciences
Science & Technology
Heteroarene
Nickel
C–O bond activation
Catalysis
Amination
C-O ACTIVATION
ARYL GRIGNARD-REAGENTS
C-O bond activation
ARYLATION
PHENOL DERIVATIVES
CROSS-COUPLING REACTIONS
NICKEL-CATALYZED AMINATION
CONSTRUCTION
ALKENYL
ELECTROPHILES
EFFICIENT
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Summary:Ni(0)/NHC-based catalyst system can promote the amination of N-heteroaryl methyl ethers via the cleavage of normally unreactive carbon–oxygen bonds. Electron-deficient N-heteroarenes including pyridine, quinoline, isoquinoline, and quinoxaline undergo amination to afford aminopyridine and related heteroarenes, which constitute an important class of compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.04.005