Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions

Bondžić, Bojan P.

doi:10.1016/j.molcata.2015.07.026

Cited by 34 publications

(39 citation statements)

References 130 publications

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“…Normally, these reactions are easier to carry out by one pot synthesis than multi-step synthesis [8]. In addition, the isolation of an intermediates are not required in MCR conditions and they are perfect candidates for drug discovery and combinatorial synthesis [9]. The most desirable potential drug candidates are libraries of small organic molecules which have limitations as bioavailable therapeutics.…”

Section: Introductionmentioning

confidence: 99%

A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies

et al. 2016

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This study deals with a new and efficient metal-free regioselective synthesis of pyrimido-fused indazoles with nitrogen ring junction motifs. We have developed a metal-free domino type reaction between 3-aminoindazole, aryl aldehydes and aceotophenones in the presence of KOH/DMF that leads to pyrimido[1,2-b]indazole analogues. Response Surface Methodology (RSM) coupled with a Box-Behnken design (BBD) were utilized for exploring the effect of base used (A), temperature of reaction (B) and (C), reaction time. This approach can allow access to a variety of pyrimidoindazole fluorophores and related compounds. The compound N,N-dimethyl-4-(2-phenylpyrimido[1,2-b]indazol-4-yl)aniline (4e) displays the maximum fluorescence intensity at 518 nm and shows a fluorescence quantum yield of 0.068. The synthesized pyramido-fused indazoles have been evaluated for their free radical scavenging activity and compound 4f showed good antioxidant activity.

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Section: Introductionmentioning

confidence: 99%

A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies

et al. 2016

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“…As aldehydes have long been used as key building blocks in heterocycle synthesis, a range of tandem hydroformylation-heterocyclisation reactions have been published. 104 By conducting hydroformylation in the presence of aryl hydrazines, a tandem hydroformylation/Fischer indole synthesis has been developed, and used by the Eilbracht group in the synthesis of a range of pharmaceutically relevant indoles (Scheme 21a). 105 The same group have used similar conditions to mimic another classical heterocycle synthesis in the form of a hydroformylation/Pictet-Spengler cascade (Scheme 21b).…”

Section: Carbonylative Processesmentioning

confidence: 99%

Homogeneous rhodium(i)-catalysis in de novo heterocycle syntheses

Neuhaus

Willis

2016

Org. Biomol. Chem.

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Recent research has led to the development of mild, efficient and selective catalytic systems based on Rh(i) complexes. This review summarises the applications of these catalysts to the synthesis of heterocycles from simple building blocks. Included herein are approaches based on cycloisomerisation, cycloaddition, hydroacylation and hydroarylation reactions, as well as various tandem and domino procedures and carbonylation processes.

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“…Nowadays, one of the ultimate goals for synthetic chemists is to mimic natural systems for the construction of complex molecules using sequential catalysis [1][2][3]. Catalytic hydroformylation has been used as a central reaction in several sequential processes to produce high-value products directly from olefins, such as alcohols, acetals, amines, and others [4][5][6][7][8][9][10][11]. We highlight the hydroformylation/acetalization reaction that allows the direct transformation of olefins into high-value oxygenated products in a sequential process without isolation of the aldehyde intermediates [12][13][14][15][16][17], including in the valorization of terpenes [18,19].…”

Section: Introductionmentioning

confidence: 99%

Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization

et al. 2021

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Two heterogeneous catalysts, MNP@SiO2-N-Xantphos/Rh(I) and MNP@SiO2-NH-C-scorpionate/Fe(II), were prepared by reaction of chloro-functionalized MNP@SiO2 with N-Xantphos and amino-functionalized MNP@SiO2 with iron(II)/C-allyl-scorpionate through nucleophilic substitution and hydroaminomethylation reactions, respectively. All catalysts were characterized using standard spectroscopic means, transmission electron microscopy (TEM), thermogravimetry (TG), and inductively coupled plasma optical emission spectrometry (ICP-OES). An active and highly selective one-pot hydroformylation/acetalization homogeneous system for the transformation of terminal and highly substituted olefins (including terpenes) onto ethyl acetals is described. A synergic effect of bimetallic Rh(I)/P and Fe(II)/C-scorpionate catalysts is disclosed for the first time. The further sequential use of the heterogeneous catalysts, MNP@SiO2-N-Xantphos/Rh(I) and MNP@SiO2-NH-C-scorpionate/Fe(II) in hydroformylation/acetalization reactions allows the direct transformation of olefin onto ethyl acetals, keeping the activity and selectivity. Both catalysts were easily recovered by magnetic separation and reused with negligible loss of activity/selectivity, after six reutilization cycles.

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Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions

Abstract: Please cite this article as: Bojan P.Bondžić, Rh catalyzed multicomponent tandem and one-pot reactions under hydroformylation conditions, Journal of Molecular Catalysis A: Chemical http://dx.

Cited by 34 publications

References 130 publications

A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies

A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies

Homogeneous rhodium(i)-catalysis in de novo heterocycle syntheses

Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization

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