Relevant bibliographies by topics / Palladium precatalysts

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Palladium precatalysts'

Author: Grafiati
Published: 4 June 2021
Last updated: 14 February 2022

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Journal articles on the topic "Palladium precatalysts"

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Takahashi, Rina, Koji Kubota, and Hajime Ito. "Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions." Chemical Communications 56, no. 3 (2020): 407–10. http://dx.doi.org/10.1039/c9cc06946a.

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A Xantphos-ligated palladium dialkyl complex can serve as a high performance precatalyst for various cross-coupling reactions, thus providing a convenient alternative to previously developed classes of precatalysts.
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Martin, Anthony R., Anthony Chartoire, Alexandra M. Z. Slawin, and Steven P. Nolan. "Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles." Beilstein Journal of Organic Chemistry 8 (September 27, 2012): 1637–43. http://dx.doi.org/10.3762/bjoc.8.187.

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The use of [Pd(NHC)(cinnamyl)Cl] precatalysts in the direct arylation of heterocycles has been investigated. Among four different precatalysts, [Pd(SIPr)(cinnamyl)Cl] proved to be the most efficient promoter of the reaction. The C–H functionalization of sulfur- or nitrogen-containing heterocycles has been achieved at low catalyst loadings. These catalyst charges range from 0.1 to 0.01 mol % palladium.
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Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Aleksandr Kostyuk, and Andrea Biffis. "Palladium(ii) complexes with chelating N-phosphanyl acyclic diaminocarbenes: synthesis, characterization and catalytic performance in Suzuki couplings." Dalton Transactions 45, no. 5 (2016): 1967–75. http://dx.doi.org/10.1039/c5dt02250a.

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Arthurs, Ross A., David L. Hughes, and Christopher J. Richards. "Planar chiral palladacycle precatalysts for asymmetric synthesis." Organic & Biomolecular Chemistry 18, no. 28 (2020): 5466–72. http://dx.doi.org/10.1039/d0ob01331e.

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Bigler, Raphael, Daniel Spiess, Joël Wellauer, Martin Binder, Victor Carré, and Serena Fantasia. "Synthesis of Biaryl Phosphine Palladium(0) Precatalysts." Organometallics 40, no. 15 (July 6, 2021): 2384–88. http://dx.doi.org/10.1021/acs.organomet.1c00288.

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Yang, Yong, Joyce Fen Yan Lim, Xinying Chew, Edward G. Robins, Charles W. Johannes, Yee Hwee Lim, and Howard Jong. "Palladium precatalysts containing meta-terarylphosphine ligands for expedient copper-free Sonogashira cross-coupling reactions." Catalysis Science & Technology 5, no. 7 (2015): 3501–6. http://dx.doi.org/10.1039/c5cy00507h.

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Novel precatalysts containing meta-terarylphosphine ligands have set a new standard for high performance and practicality in copper-free Sonogashira cross-coupling catalysis using simple and reliable protocols.
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Vásquez-Céspedes, Suhelen, Michael Holtkamp, Uwe Karst, and Frank Glorius. "Reusable and Magnetic Palladium and Copper Oxide Catalysts in Direct ortho and meta Arylation of Anilide Derivatives." Synlett 28, no. 20 (May 2, 2017): 2759–64. http://dx.doi.org/10.1055/s-0036-1589007.

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We report a general, direct C–H arylation of anilide derivatives using reusable palladium or copper oxide on magnetite as heterogeneous precatalysts. Highly selective ortho and meta arylations are achieved using electronically and sterically diverse diaryliodonium salts. Catalytically active soluble species from the heterogeneous precursors were detected by experimental techniques. Preliminary mechanistic investigation suggests different reaction pathways for each of the catalysts.
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Jahnke, Mareike C., Tania Pape, and F. Ekkehardt Hahn. "Molecular Structures and Catalytic Activity of Palladium Complexes Derived from Lutidine-bridged Bis(benzimidazolin-2-ylidene) Ligands." Zeitschrift für Naturforschung B 62, no. 3 (March 1, 2007): 357–61. http://dx.doi.org/10.1515/znb-2007-0308.

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Reaction of lutidine-bridged dibenzimidazolium dibromides 1 - 4 with palladium acetate gives pincer-type palladium complexes of the type [Pd(L)Br]Br [5]Br-[8]Br. Crystals suitable for an X-ray diffraction study have been obtained by slow evaporation of the solvent from dichloromethane/methanol solutions of [7]Br and [8]Br. The crystal structure of [7]+ reveals a pincer topology of the cationic complex with a distorted square-planar coordination geometry at the metal center. From a solution of complex [8]Br, a dinuclear byproduct [9]+ was obtained with two bis(benzimidazolin- 2-ylidene) ligands coordinating in a bridging fashion. The pincer-type palladium complexes [5]Br- [8]Br were tested as precatalysts in Suzuki coupling reactions.
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Zhang, Fei-Yi, Xiao-Bing Lan, Chang Xu, Hua-Gang Yao, Tian Li, and Feng-Shou Liu. "Rigid hindered N-heterocyclic carbene palladium precatalysts: synthesis, characterization and catalytic amination." Organic Chemistry Frontiers 6, no. 18 (2019): 3292–99. http://dx.doi.org/10.1039/c9qo00726a.

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Rigid hindered N-heterocyclic carbene palladium complexes have been developed and exhibited high activities for a variety of (hetero)aryl chlorides with (hetero)anilines and amines under aerobic conditions.
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Biffis, Andrea, Elena Scattolin, Nicoletta Ravasio, and Federica Zaccheria. "Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions." Tetrahedron Letters 48, no. 49 (December 2007): 8761–64. http://dx.doi.org/10.1016/j.tetlet.2007.10.005.

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Dissertations / Theses on the topic "Palladium precatalysts"

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Bruno, Nicholas C. (Nicholas Charles). "Novel palladium precatalysts and their application in cross- coupling reactions and copper-catalyzed enantioselective ring formation." Thesis, Massachusetts Institute of Technology, 2015. http://hdl.handle.net/1721.1/98821.

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Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2015.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Chapters 1 - 3. A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with improved solution stability and that are readily prepared from a wider range of phosphine ligands, including the bulky, electron-rich di-tert-butylphosphino biaryl ligands. Additionally, N-methyl- and N-phenyl analogues have been prepared. These efficacy of these precatalysts were examined in a broad range of C-C, C-N, and C-O bond-forming reactions. Chapter 4. The intramolecular hydroalkylation of di- and trisubstituted alkenes bearing a pendant alkyl bromide to form stereodefined (hetero)carbocycles is reported. The system is highly regio- and stereoselective and employs a Cu-DTBM-SEGPHOS catalyst and (dimethoxy)methylsilane as the stoichiometric reductant. This intramolecular hydroalkylation reaction provides facile access to a multitude of ring systems and its utility is further demonstrated in the enantioselective synthesis of paroxetine.
by Nicholas C. Bruno.
Ph. D. in Organic Chemistry
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2

Beck, John Frederick. "orthoMetallated Acetophenone Imines as Ligands for Transition and Main Group Metals: Synthesis and Organometallic Reactivity and the Hydroamination of Allenes using a Palladium Allyl Triflate 3-Iminophosphine Precatalyst." University of Toledo / OhioLINK, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1311613955.

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NORTON, DANIELLE. "A new, improved precatalyst for Suzuki-Miyaura cross-coupling reactions." Thesis, 2009. http://hdl.handle.net/1974/1995.

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Carbon-carbon bond formation is one of the most important reactions in organic chemistry, and the Suzuki-Miyaura cross-coupling reaction has become a forerunner in this area. Considerable research has been directed at the mechanistic aspects and synthetic utility of the reaction; however, little attention has been given to the formation of the putative PdL2 catalysts. Due to their high reactivities, these catalysts are typically difficult to store and therefore are often generated in situ in unknown yields and at unknown rates via any number of available palladium precursors. This thesis describes research directed towards determining the optimum conditions to quantitatively generate compounds of the type Pd(0)Ln (L = PMePh2, PPh3, PCy3, PMeBut2, PBut3, dppe, dppp, dppf) from Pd(h5-C5H5)(h3-1-Ph-C3H4). Pd(h5-C5H5)(h3-1-Ph-C3H4) has been found to be a superior precursor for synthesizing catalytically active PdL2 compounds due to its ease in handling and reactivity with tertiary phosphines. Furthermore, investigations into the role of water in the transmetallation step of the Suzuki-Miyaura reaction are presented. The research indicates that water is necessary to effect the transmetallation step when coupling [NBu4][PhBF3] with 4-bromotoluene in toluene; however, the amount of water above one equivalent has no significant effect on the rate or yield of the reaction.
Thesis (Master, Chemistry) -- Queen's University, 2009-07-23 12:57:10.248
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Winston, Matthew Steven. "Chemistry of PNP Bis(phosphide) Pincer Ligands and Palladium(II) Dimers as Robust, Versatile Precatalysts for Olefin Isomerization, Oligomerization, and Oxidation." Thesis, 2013. https://thesis.library.caltech.edu/7225/1/MSW_Thesis.pdf.

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The first half of this thesis details the synthesis and coordination chemistry of a very unusual pyridine-linked bis(secondary phosphine) pincer ligand system. Despite the highly nucleophilic phosphide donors, this dianionic system is an unexpectedly poor pincer ligand. Crystallographic and DFT studies reveal that both phosphide-metal σ- and π-bonding is compromised by long metal-phosphorus bonds, which result in significant distortions to the chelate ring. The neutral ligand coordinates readily κ2 (via phosphines) to late metals, such as palladium(II), affording P-chirogenic diastereomers. Crystallographic and spectroscopic analysis of a series of palladium(II) dihalides stabilized by this bis(phosphine) indicate that one diastereomer is enthalpically favored, while the other more structurally versatile diastereomer is favored entropically. There is also evidence of an interesting phosphine epimerization pathway assisted by the non-coordinated pyridine ring.

Ethylene polymerization and ethylene/1-hexene copolymerization activities of several zirconium(IV) and vanadium(III) polymerization precatalysts supported by heterocycle-linked bis(phenolate) ligands are also discussed. Activities as high as 106 g PE/(mol x h) were observed, but only the vanadium catalyst incorporates comonomer, albeit with low efficiency (<1 mol%).

Finally, catalytic applications of air- and water-tolerant bis(μ-hydroxy) palladium(II) dimers have been investigated. Mechanistic studies show that this precatalyst can oxygenate olefins via a Wacker-type mechanism upon dimer dissociation. In the absence of stoichiometric oxidant, the resulting palladium(II) hydride intermediate can then isomerize and oligomerize olefins with turnover numbers at room temperature as high as 2100/h and 600/h, respectively. We also show that the catalyst is insensitive to water and air, so that olefin isomerization and oligomerization can be carried out on the benchtop in the absence of activators. In the presence of excess tert-butylhydroperoxide, Wacker-type behavior is favored, and neither isomerization nor oligomerization is observed. These dimers can also catalyze the aerobic dehydrogenation of cyclohexene to benzene with relatively low turnover numbers (1/h). Nevertheless, mechanistic studies indicate a C-H activation/β-hydride elimination sequence that does not involve an allylic-activated species.

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Book chapters on the topic "Palladium precatalysts"

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Huang, Lin, and Pui Kwan Wong. "Nature of the True Catalytic Species in CarbonCarbon Coupling Reactions with Heterogeneous Palladium Precatalysts." In Palladium-Catalyzed Coupling Reactions, 387–408. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527648283.ch10.

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Maestri, G., and A. Serafino. "1.14 Palladium(I)-Mediated Reactions." In Free Radicals: Fundamentals and Applications in Organic Synthesis 1. Stuttgart: Georg Thieme Verlag KG, 2021. http://dx.doi.org/10.1055/sos-sd-234-00313.

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AbstractSeveral elegant reactivities can be observed in reactions involving palladium(I) species, allowing access to molecular architectures that are often beyond the capabilities of popular diamagnetic palladium complexes. This review presents three main axes of research in this context, which have mostly emerged in the last decade. Reactions promoted by visible light enable synthetic methods that are unusual in their mild experimental conditions coupled with remarkably broad functional group tolerance. The use of discrete palladium(I) dimers as precatalysts allows one to perform a wide set of cross-coupling protocols, such as Kumada and Negishi reactions, and chalcogenation reactions, with a surgical precision on the carbon—halogen bond that is initially activated. The generation of alkyl radicals and palladium(I) species through a thermal strategy proves useful for the elaboration of substrates with several polyfluorinated fragments, which are otherwise elusive coupling partners for more common two-electron processes.
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