Tuning the hydrogen donor/acceptor behavior of ionic liquids in Pd-catalyzed multi-step reactions

López-Vinasco, Angela M.; Guerrero‐Ríos, Itzel; Favier, Isabelle; Pradel, Christian; Teuma, Emmanuelle; Gómez, Montserrat; Martin, Erika

doi:10.1016/j.catcom.2014.10.011

Cited by 12 publications

(8 citation statements)

References 21 publications

(30 reference statements)

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“…As expected, nitrobenzene gave aniline in quantitative yield (entry 1, Table 3). PdB was also an efficient catalyst for the reduction of carbonyl groups, coming from both aldehydes (12)(13)(14) and ketones (15)(16)(17). Concerning the formyl groups, benzaldehyde derivatives exhibiting substituents inducing different electronic effects, were fully converted into the corresponding benzyl alcohols under smooth conditions (3 bar H2; entries 2-4, Table 3).…”

Section: Pd-catalyzed Hydrogenation Reactionsmentioning

confidence: 99%

“…In our group, PdNPs stabilized by [BMI][PF6] have been generated in previous studies leading to high catalytic activity in Suzuki cross-coupling reaction without palladium leaching up to ten cycles [10,11]. In this frame, in particular, PdNPs stabilized by thioether-phosphine ligands had been used as catalytic precursors in Heck-Mizoroki cross-coupling and C=C hydrogenation reactions [12]. However, the above-mentioned ILs have environmental concerns, which consequently led to the search of an environmental friendly medium.…”

Section: Introductionmentioning

confidence: 99%

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Palladium nanoparticles stabilized by novel choline-based ionic liquids in glycerol applied in hydrogenation reactions

et al. 2020

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Palladium nanoparticles stabilized by choline-based ionic liquids in glycerol were prepared from Pd(II) precursors by simply heating at 80 °C under argon; in this process, the water present in the ionic liquid was found to be the responsible for the reduction of Pd(II) into zero-valent palladium species. Palladium nanoparticles were fully characterized in both liquid phase and solid state. The as-prepared metal nanoparticles exhibited remarkable catalytic activity in hydrogenation processes for a significant variety of functional groups (alkenes, alkynes, nitro derivatives, benzaldehydes, aromatic ketones). Highlights  Palladium nanoparticles in glycerol stabilized by novel choline-based ionic liquids.  Characterization of palladium nanoparticles both in solid and liquid phase.  Palladium nanoparticles showing high catalytic activity in hydrogenation reactions.  Selective hydrogenations for non-conjugated alkynes.  Efficient reduction of carbonyl derivatives.

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Section: Pd-catalyzed Hydrogenation Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Palladium nanoparticles stabilized by novel choline-based ionic liquids in glycerol applied in hydrogenation reactions

et al. 2020

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“…Moreover, β‐substituted carbonyl compounds are the backbone of active biomolecules, such as enokipodine B (fungal biomarker) or paroxetine (antidepressant) . Synthetic methods used for the preparation of β‐arylketones are usually based on a coupling between methyl vinyl ketone (MVK) and various aryl reagents in the presence of palladium catalysts . Further functionalization, leading to appropriate β‐diarylketones, can be performed using synthetic tools that form a new carbon–carbon bond: the Heck reaction or the reductive Heck reaction (conjugate addition) .…”

Section: Introductionmentioning

confidence: 99%

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Wirwis

Trzeciak

2019

Applied Organom Chemis

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Two efficient Pd‐catalyzed tandem pathways for the synthesis of 4,4‐diaryl‐2‐butanones and 4,4‐diaryl‐3‐buten‐2‐ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4‐aryl‐3‐buten‐2‐one with the yield of up to 92% in 1 hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4‐diaryl‐3‐buten‐2‐ones in high yield. Reaction selectivity changed completely to saturated 4,4‐diaryl‐2‐butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4 hr), using 0.5 mol% of the Pd (OAc)2 catalyst without additional ligands.

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“…The reduction of the exocyclic C=C double-bond occurred without the need of external molecular hydrogen, strongly suggesting a hydrogen-transfer reaction catalyzed by a Pd-hydride species formed during molecular-type Heck coupling, thanks to the basic behavior of the IL anion, methyl hydrogenphosphonate. Later, we were interested in how to design an ionic liquid with the aim of promoting the transfer hydrogenation, assisted by PdNPs [119]. PdNPs stabilized with thioetherphosphine ligands were prepared in [EMI][MeHPO3].…”

Section: Multi-step Cross-coupling/reduction Reactionsmentioning

confidence: 99%

“…By comparison to other ionic liquids, it was proven that [EMI][MeHPO3] was actually playing the role of hydrogen source at high temperature; at low temperatures, it behaves as a hydrogen acceptor (Figure 9). Later, we were interested in how to design an ionic liquid with the aim of promoting the transfer hydrogenation, assisted by PdNPs [119]. PdNPs stabilized with thioetherphosphine ligands were prepared in [EMI][MeHPO 3 ].…”

Section: Multi-step Cross-coupling/reduction Reactionsmentioning

confidence: 99%

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

et al. 2021

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Metal nanoparticles have been deeply studied in the last few decades due to their attractive physical and chemical properties, finding a wide range of applications in several fields. Among them, well-defined nano-structures can combine the main advantages of heterogeneous and homogenous catalysts. Especially, catalyzed multi-step processes for the production of added-value chemicals represent straightforward synthetic methodologies, including tandem and sequential reactions that avoid the purification of intermediate compounds. In particular, palladium- and copper-based nanocatalysts are often applied, becoming a current strategy in the sustainable synthesis of fine chemicals. The rational tailoring of nanosized materials involving both those immobilized on solid supports and liquid phases and their applications in organic synthesis are herein reviewed.

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Tuning the hydrogen donor/acceptor behavior of ionic liquids in Pd-catalyzed multi-step reactions

Cited by 12 publications

References 21 publications

Palladium nanoparticles stabilized by novel choline-based ionic liquids in glycerol applied in hydrogenation reactions

Palladium nanoparticles stabilized by novel choline-based ionic liquids in glycerol applied in hydrogenation reactions

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

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