Copper Catalyzed Decarboxylative Functionalization of Ketoacids

Quintard, Adrien

doi:10.1002/tcr.202100045

Cited by 5 publications

(2 citation statements)

References 92 publications

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“…The aqueous H 2 O 2 , as an inorganic oxidant, displayed a major action in the conversion and formation of the target product, as reported elsewhere. 70 Hence, using an organic oxidant for the catalytic reaction was an essential demand to demonstrate the nature of the oxidant in the catalytic system; tert-butyl hydroperoxide (70% aqueous t BuOOH, 6.5 mmol) was probed as an external oxidant.…”

Section: Catalystmentioning

confidence: 99%

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Adam,

Taha,

Hereba

et al. 2024

Applied Organom Chemis

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Based on the strong coordination ability of substituted imines towards transition metals of different oxidation states, the coordination of the HL imine ligand with the Cu2+ ion to form the Cu–bis–imine complex was achieved in 2:1 molar ratios. Their structures were confirmed with various spectroscopic tools. Heterogeneously, CuL2 was successfully appended on ZnO@TiO2 nanoparticles, as the less harmful materials, within the deprotonated p‐hydroxy chain of the bonded ligand in CuL2. The surface and internal structural morphologies of ZnO@TiO2@CuL2 were analyzed using X‐ray diffraction (XRD), field‐emission scanning electron microscopy (FESEM), high‐resolution transmission electron microscopy (HRTEM), energy‐dispersive X‐ray spectroscopy (EDS), and infrared (IR) spectroscopy, in addition to thermogravimetric analysis (TGA). The catalytic behavior of both catalysts, CuL2 (the homogeneous catalyst) and ZnO@TiO2@CuL2 (the heterogeneous catalyst), was examined in the benzyl alcohol redox protocols using H2O2 for their optimization. α,β‐Cinnamic acid decarboxylative bromination in the presence of potassium bromide and H2O2 in water was studied with both catalysts, in which (2‐bromovinyl)benzene was the chemoselective product. Both Cu catalysts displayed appreciable catalytic effectiveness for the oxidation protocols and the decarboxylative bromination reactions. CuL2 recorded less required time for optimization than that of the heterogeneous catalyst. The catalytic effectiveness of CuL2 was less promoted than that of ZnO@TiO2@CuL2. Despite the less performance in yield of benzaldehyde for the oxidation protocols with ZnO@TiO2@CuL2, ZnO@TiO2@CuL2 had more recycling than its homogeneous counterpart, with seven to three times, respectively.

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Section: Catalystmentioning

confidence: 99%

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Adam,

Taha,

Hereba

et al. 2024

Applied Organom Chemis

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“…Carboxylic acids possessing adjacent electron-withdrawing groups have long been known for their propensity to decarboxylate relatively easily. , These properties have been applied with success in catalyzed transformation to introduce different functionalities while generating one equivalent of gaseous CO 2 as the single waste (Scheme a). − Taking advantage of these attributes, one can envisage a temporary protonation of basic functions such as primary or secondary amines (Scheme b) . After formation of the ammonium ion, the time-controlled catalyzed trichloroacetate decarboxylation generates a transient chloroform anion, protonated rapidly by the ammonium salt, thus triggering the return to the neutral amine.…”

Section: Trichloroacetic Acid As Chemical Fuel For Conformational Swi...mentioning

confidence: 99%

Out of Equilibrium Chemical Systems Fueled by Trichloroacetic Acid

Olivieri

Quintard

2022

ACS Org. Inorg. Au

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Dissipative systems are based on the supply of energy to a system by fuel pulses and dissipation of this energy through the fuel decomposition, resulting in repetition of a given physical or biological function. Such out of equilibrium processes are at the heart of all living organisms, and in the past decade, researchers have attempted to transpose these principles to purely synthetic systems. However, upon fuel decomposition, the resulting waste generated tends to accumulate in the system, rapidly inhibiting the machinery after a few cycles of fuel pulses. In order to solve this issue, trichloroacetic acid has appeared as a fuel of choice to reversibly change the acidity of a system, liberating volatile chloroform and CO2 upon fuel decomposition. In this Perspective, we present the advantages of this fuel and successful applications ranging from conformational switches to rotary motors to temporal control over crystallization or smart materials.

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Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter

et al. 2022

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The enantioselective construction of fluorohydrins featuring a tetrasubstituted stereocenter embedded in complex frameworks represents an important challenge. Herein, we report a multicatalytic strategy enabling the stereoselective preparation of a new type of scaffold containing such a challenging fluorohydrin motif. The sequence is based on an organocatalyzed fluorination of α‐disubstituted aldehydes followed by a diastereoselective copper‐catalyzed decarboxylative aldol reaction. Reduction of the generated β‐hydroxy ketone followed by a Lewis base‐catalyzed kinetic resolution enables the isolation of original fluorinated 1,3‐diols with perfect diastereo‐ and enantio‐control.

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Copper Catalyzed Decarboxylative Functionalization of Ketoacids

Cited by 5 publications

References 92 publications

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Out of Equilibrium Chemical Systems Fueled by Trichloroacetic Acid

Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter

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Copper Catalyzed Decarboxylative Functionalization of Ketoacids

Cited by 5 publications

References 92 publications

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO2 nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO2 nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Out of Equilibrium Chemical Systems Fueled by Trichloroacetic Acid

Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter

Contact Info

Product

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About

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination

Immobilized transition metal (II) bis–imine chelate on ZnO@TiO₂ nanoparticles as sufficient catalysts for alcohol oxidation and for α,β‐cinnamic acid decarboxylative bromination