Palladium-catalyzed oxidative three-component tandem annulation reaction: Access to polysubstituted pyrroles

•Synthesis of polysubstituted pyrroles using readily available substrates.•Wide variety of products with good to excellent yield.•No need for active acetylenic compounds.•No need for a directing group on nitrogen. Pd-catalyzed domino processes involving CC/CN coupling of in situ generated enaminones...

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Bibliographic Details
Published in:Molecular catalysis 2024-06, Vol.562, p.114195, Article 114195
Main Authors: Bashkar, Mohammad, Nowrouzi, Najmeh
Format: Article
Language:English
Subjects:
1,3-dicarbonyl compound
Amine
Diphenylacetylene
Palladium-catalyzed
Pyrrole
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Summary:•Synthesis of polysubstituted pyrroles using readily available substrates.•Wide variety of products with good to excellent yield.•No need for active acetylenic compounds.•No need for a directing group on nitrogen. Pd-catalyzed domino processes involving CC/CN coupling of in situ generated enaminones with alkynes in the absence of a directing group on nitrogen has been developed. In this protocol, linear and cyclic 1,3-diketones in the reaction with aliphatic amines and diphenylacetylene derivatives provides efficient access to substituted pyrroles through Pd-catalyzed CH activation of enaminones. Using aromatic amines instead of aliphatic amines does not accomplish this organic transformation due to the formation of carbazolone. In this method, there is no need for active acetylene compounds, and also, unlike a number of previously reported methods, the reaction is performed without the presence of a directing group on nitrogen, thus highlighting a useful synthetic application of the present catalytic protocol. [Display omitted]
ISSN:2468-8231
2468-8231
DOI:10.1016/j.mcat.2024.114195