Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu, Xiang; Astruc, Didier

doi:10.1002/adsc.201800343

Cited by 92 publications

(39 citation statements)

References 480 publications

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“…To retain the double bonds for future further functionalizations, we became interested in other reducing procedures and optimized them with nitrile 2 b derived from o ‐toluic acid (Table 3). Catalytic hydrogenation with palladium on charcoal, a common and cheap catalyst, [24] gave full conversion, but only one double bond was reduced (entry 1). On the other hand, rhodium on alumina, which has been applied for the synthesis of lactams from nitriles, [25] gave no conversion (entry 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Krüger

Linker

2021

Eur J Org Chem

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A convenient method for the synthesis of γ‐spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl‐substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new γ‐spirolactams have been synthesized in analytically pure form.

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Section: Resultsmentioning

confidence: 99%

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Krüger

Linker

2021

Eur J Org Chem

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“…3 The ascertained versatility of palladium can be attributed to its ability to stabilize a large variety of matter states at different oxidations states, by appropriate tuning of conditions: organometallic complexes, nanoparticles, and extended surfaces, including polymetallic materials; furthermore, these different Pd-based species have proven their compatibility with different types of solids, permitting their immobilization and in consequence their recycling, aspect of foremost importance in the frame of developing sustainable industrial processes. [4][5][6] Concerning palladium nanoparticles, Bönnemann 7 and Reetz 8 independently described the first syntheses of palladium nanocatalysts in conventional organic solvents prepared by bottom-up (palladium salt chemical reduction) and top-down (electrochemical process transforming palladium bulk into palladium nanoparticles), respectively, for applications in C-C crosscoupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles in Polyols: Synthesis, Catalytic Couplings, and Hydrogenations

2019

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Alcohols, in particular polyols, are well-known for the synthesis of metal nanoparticles often acting as reducing agents, solvents, and stabilizers. Given not only their structural flexibility depending on the number of OH functions and their inherent H bonding interactions, but also the wide range of polyol molecular weights readily available, different physico-chemical properties (boiling point, polarity, viscosity) could be exploited towards the synthesis of well-defined nanomaterials. In particular, the relevance of the supramolecular structure of polyols has a fundamental impact on the formation of metal nanoparticles thereby favoring the dispersion of the nanoclusters. In the field of the metal-based nanocatalysis, palladium occupies a privileged position mainly due to its remarkable versatility in terms of reactivity representing a foremost tool in synthesis. In this review, we describe the controlled synthesis of Pd-based nanoparticles in polyol medium focusing on the progress in terms of tailoring size, morphology, structure, and surface state. Moreover, we discuss the use of 4.2. C(sp)-C(sp 2) Sonogashira cross-coupling 4.3. C(sp 2)-C(sp 2) Hiyama-Denmark cross-coupling 4.4. C(sp 2)-C(sp 2) Heck-Mizoroki cross-coupling 4.5. C(sp 2)-C(sp 2 /sp 3) Suzuki-Miyaura cross-coupling 4.5.1. In PEG and glycerol media 4.5.2. Solid-supported nanocatalysts 4.6. C(sp 2)-C(sp 2)-C(sp 2) Carbonylative Suzuki cross-coupling 4.7. C(sp 2)-C(sp 2) Ullmann-type homo-coupling 4.8. Miscellaneous: SiN and C-N amination reactions 5. Conclusions and outlook

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“…Palladium nanoparticles deposited on the carbon surface are among the most demanded substances extensively studied by electron microscopy. As heterogeneous Pd/carbon catalysts, they are ubiquitously used in organic synthesis for production of drugs, pharmaceutical substances and molecular electronics devices [9][10][11][12] . Large scale production of Pd/C catalysts is utilized in industry.…”

Section: Background and Summarymentioning

confidence: 99%

Electron microscopy dataset for the recognition of nanoscale ordering effects and location of nanoparticles

et al. 2020

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A unique ordering effect has been observed in functional catalytic nanoscale materials. Instead of randomly arranged binding to the catalyst surface, metal nanoparticles show spatially ordered behavior resulting in formation of geometrical patterns. Understanding of such nanoscale materials and analysis of corresponding microscopy images will never be comprehensive without appropriate reference datasets. Here we describe the first dataset of electron microscopy images comprising individual nanoparticles which undergo ordering on a surface towards the formation of geometrical patterns. The dataset developed in this study spans three levels of nanoscale organization: (i) individual nanoparticles (1-5 nm) and arrays of nanoparticles (5-20 nm), (ii) ordering effects (20-200 nm) and (iii) complex patterns (from nm to μm scales). The described dataset for the first time provides a possibility for the development of machine learning algorithms to study the unique phenomena of nanoparticles ordering and hierarchical organization.

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Development of the Applications of Palladium on Charcoal in Organic Synthesis

Cited by 92 publications

References 480 publications

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Palladium Nanoparticles in Polyols: Synthesis, Catalytic Couplings, and Hydrogenations

Electron microscopy dataset for the recognition of nanoscale ordering effects and location of nanoparticles

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