Iron/TEMPO-catalyzed direct aerobic oxidative coupling of methyl-mubstituted N-heteroazaarenes with alcohols

An iron/TEMPO catalyzed aerobic oxidative coupling reaction of methyl-substituted N-heteroazaarenes with alcohols afforded various E-disubstituted olefins in good to excellent yields under mild condition with H2O as sole byproduct. [Display omitted] •Water as sole byproduct.•Mild conditions, without...

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Published inTetrahedron letters Vol. 61; no. 21; pp. 151885 - 151888
Main Authors Zhang, Zhiguang, Ma, Yantao, Dai, Siwei, Li, Ling, Zhang, Yong, Li, Hao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.05.2020
Elsevier
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Summary:An iron/TEMPO catalyzed aerobic oxidative coupling reaction of methyl-substituted N-heteroazaarenes with alcohols afforded various E-disubstituted olefins in good to excellent yields under mild condition with H2O as sole byproduct. [Display omitted] •Water as sole byproduct.•Mild conditions, without any ligands.•Readily available starting materials. A novel direct oxidative coupling of methyl-substituted N-heteroazaarenes with alcohols has been developed to construct olefins under mild condition. The reaction is catalyzed by Fe(NO3)3·9H2O/TEMPO with oxygen as terminal oxidant. A variety of E-disubstituted olefins bearing diverse functional groups could be obtained selectively in moderate to excellent yields. The reaction is environmentally friendly and ligand-free.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151885