Journal ArticleDOI
Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations.
TLDR
Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines by tolerating a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substitution at the 4-position via lithiation or halogenation.Abstract:
Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available β-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.read more
Citations
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Recent Advances in the Construction of Phosphorus-Substituted Heterocycles, 2009–2019
Journal ArticleDOI
Synthesis of Polysubstituted Pyrroles from Activated Alkynes and N-Propargylamines through Base-Catalyzed Cascade Reaction
TL;DR: A novel K3PO4-catalyzed synthesis of polysubstituted pyrroles by a Michael addition/alkyne carbocyclization of activated alkynes and N-propargylamines has been developed.
Journal ArticleDOI
Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3–H bonds
TL;DR: A Rh(iii)-catalyzed cross-coupling/cyclization cascade of α-imino Csp(3)-H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed, offering an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
Journal ArticleDOI
The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem Three-Component Reaction
Xue-Qing Mou,Zheng-Liang Xu,Li Xu,Shao-Hua Wang,Bang-Hong Zhang,Di Zhang,Jie Wang,Wei-Ting Liu,Wen Bao +8 more
TL;DR: This reaction not only reveals a new reaction mode for α-aminonitriles, but also provides a new and efficient cyclization pattern for the synthesis of multisubstituted pyrroles as well as their derivatives, which might facilitate related biological studies.
Journal ArticleDOI
Catalyst-Controlled C–C σ Bond Cleavages in Metal Halide-Catalyzed Cycloisomerization of 3-Acylcyclopropenes via a Formal 1,1-Halometalation Mechanism: Insights from Quantum Chemical Calculations
Genping Huang,Yuanzhi Xia +1 more
TL;DR: In this paper, the authors investigated the origin of divergent regiochemistry of cyclopropenyl ketones with different metal halide catalysts using quantum chemical calculations and found that a novel mechanism involving a formal 1,1-halometalation is the energetically most favorable one.
References
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Coinage Metal-Assisted Synthesis of Heterocycles
TL;DR: The chiral stationary phase for Heterocycloaddition showed good chiral recognition ability towards various racemates, including N/O-Vinylation/Arylation and Radical Cyclization of Haloalkenes and Haloalkynes.
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Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles
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Multicomponent reactions for the synthesis of pyrroles
TL;DR: Multicomponent reactions are one of the most interesting concepts in modern synthetic chemistry and provide an attractive entry into pyrrole derivatives, which are very important heterocycles from many points of view.
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