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
Subjects
Aerobic oxidation
Alcohols
Azaarenes
Chemistry
Chemistry, Organic
Olefination
Physical Sciences
Science & Technology
Azaarenes
Olefination
Aerobic oxidation
Alcohols
DIRECT ALKENYLATION
ALKYLATION
ALPHA-FUNCTIONALIZATION
WITTIG OLEFINATION
ALDEHYDES
C(SP)-H FUNCTIONALIZATION
HETEROCYCLES
AMINES
TEMPO
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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