Synthesis of Highly Substituted Pyrroles via Nucleophilic Catalysis

Ngwerume, Simbarashe; Camp, J. E.

doi:10.1021/jo1011448

Cited by 70 publications

(41 citation statements)

References 16 publications

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“…Dimethyl 5-(4-bromophenyl)-1H-pyrrole-2,3-dicarboxylate was synthesised as described previously. [15] The linker units were introduced by Suzukic oupling reactions with 4-formylphenyl and 5-formyl-2-thienyl boronic acids with yields of 74 %a nd 87 %r espectively.F or dye 1 the anchor groups were first hydrolysed by refluxing in basic methanolf ollowed by condensation of malononitrile. For dyes 2 and 3 the bodipyg roups were introduced through ac ondensation reaction with 2,4-dimethyl-3-ethylpyrrole, oxidation with p-chloranil and subsequent coordination of boron trifluoride etherate.…”

Section: Synthesismentioning

confidence: 99%

Resonance Raman Study of New Pyrrole‐Anchoring Dyes for NiO‐Sensitized Solar Cells

et al. 2017

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Three dyes for p-type dye-sensitised solar cells containing a novel doubly anchored pyrrole donor group were synthesised and their solar cell performances were evaluated. Dye 1 was comprised of a phenyl-thiophene linker and a maleonitrile acceptor, which has been established as an effective motif in other push-pull dyes. Two boron dipyrromethane analogues, dyes 2 and 3, were made with different linker groups to compare their effect on the behaviour of these dyes adsorbed onto nickel oxide (dye|NiO) under illumination. The photoexcited states of dye|NiO were probed using resonance Raman spectroscopy and compared to dyes anchored using the conventional 4-aminobenzoic acid moiety (P1 and 4). All three components, the anchor, the linker and the acceptor group were found to alter both the electronic structure following excitation and the overall solar cell performance. The bodipy acceptor gave a better performance than the maleonitrile acceptor when the pyrrole anchor was used, which is the opposite of the triphenylamine push-pull dyes. The linker group was found to have a large influence on the short-circuit current and efficiency of the p-type cells constructed.

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Section: Synthesismentioning

confidence: 99%

Resonance Raman Study of New Pyrrole‐Anchoring Dyes for NiO‐Sensitized Solar Cells

et al. 2017

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“…We also developed a gold‐catalysed synthesis of highly substituted pyrroles 11 (Scheme ) , . Starting from oximes 5 , activation of either ethylpropiolate ( 6 ) or dimethylacetylene decarboxylation ( 7 ) with the in situ formed cationic gold species allowed for facile formation of O ‐vinyloximes 8 .…”

Section: Auto‐tandem Catalysis Approaches To Heterocyclesmentioning

confidence: 99%

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Camp

2016

Eur J Org Chem

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Auto‐tandem catalysis (ATC) is a powerful method for the synthesis of heterocycles and carbocycles as well as acyclic compounds. The process is defined as a single reagent catalysing multiple, mechanistically distinct processes of a chemical reaction. In this review recent advances in ATC using transition metal catalysts is described. In particular, the use of different catalytic systems for the controlled synthesis of the desired product, enantioselective synthesises in which multiple bonds are formed and mechanistic investigations are illustrated with applications to the synthesis of heterocycles and carbocycles as well as acyclic compounds. New approaches that use earth abundant catalysts, greener solvents or increased catalyst efficiency are highlighted. Examples of ATC reaction development are also included. In addition, ATC processes are used as key steps in the synthesis of natural products as well as biologically active compounds.

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“…This method can serve as an excellent alternative of existing 3H-pyyrrole syntheses (Scheme 15). A first report On regioselective intermolecular addition of in situ generated O-vinyl oximes to activated alkynes in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) followed by thermal rearrangement has been reported by Ngwerume et al [54], which lead to the formation of pyrrole derivatives 51 through a one-pot assembly (Scheme 17).…”

Section: Synthesis Of Pyrrolesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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Synthesis of Highly Substituted Pyrroles via Nucleophilic Catalysis

Cited by 70 publications

References 16 publications

Resonance Raman Study of New Pyrrole‐Anchoring Dyes for NiO‐Sensitized Solar Cells

Resonance Raman Study of New Pyrrole‐Anchoring Dyes for NiO‐Sensitized Solar Cells

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

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