Iron-catalyzed intermolecular cycloaddition of diazo surrogates with hexahydro-1,3,5-triazines

We report here an unprecedented iron-catalyzed cycloaddition reaction of diazo surrogates with hexahydro-1,3,5-triazines, providing five-membered heterocycles in moderate to high yields under mild reaction conditions. This cycloaddition features C-N and C-C bond formation using a cheap iron catalyst...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 15; no. 37; pp. 7743 - 7746
Main Authors Liu, Pei, Zhu, Chenghao, Xu, Guangyang, Sun, Jiangtao
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 26.09.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
MECHANISTIC INSIGHTS
COMPLEXES
CARBENE INSERTION
CYCLOPROPANATION
BOND FORMATION
METAL-FREE
ETHYL DIAZOACETATE
N-TOSYLHYDRAZONES
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Summary:We report here an unprecedented iron-catalyzed cycloaddition reaction of diazo surrogates with hexahydro-1,3,5-triazines, providing five-membered heterocycles in moderate to high yields under mild reaction conditions. This cycloaddition features C-N and C-C bond formation using a cheap iron catalyst. Importantly, different to our former report on a gold-catalyzed system, both donor/donor and donor/acceptor diazo substrates are tolerated in this iron-catalyzed protocol.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02115a