Category: 53199-31-8

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Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates

Difficulties associated with handling H2 and CO in metal-catalyzed processes have led to the development of chemical surrogates to these species. Despite many successful examples using this strategy, the application of convenient hydrogen halide (HX) surrogates in catalysis has lagged behind considerably. We now report the use of ammonium halides as HX surrogates to accomplish a Pd-catalyzed hydrohalogenation of enynes. These safe and practical salts avoid many drawbacks associated with traditional HX sources including toxicity and corrosiveness. Experimental and computational studies support a reaction mechanism involving a crucial E-to-Z vinyl-Pd isomerization and a carbon-halogen bond-forming reductive elimination. Furthermore, rare examples of C(sp3)-Br and ?Cl reductive elimination from Pd(II) as well as transfer hydroiodination using 1-iodobutane as an alternate HI surrogate are also presented.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride

Palladium-catalyzed hydroaminocarbonylation of alkenes for the synthesis of primary amides has long been an elusive aim. Here, we report an efficient catalytic system which enables inexpensive NH4Cl to be utilized as a practical alternative to gaseous ammonia for the palladium-catalyzed alkene-hydroaminocarbonylation reaction. Through appropriate choice of the palladium precursors and ligands, either branched or linear primary amides can be obtained in good yields with good to excellent regioselectivities. Primary mechanistic studies were conducted and disclosed that electrophilic acylpalladium species were capable of capturing the NH2-moiety from ammonium salts to form amides in the presence of CO with NMP as a base.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments. Safety of Bis(tri-tert-butylphosphine)palladium. Introducing a new discovery about 53199-31-8, Name is Bis(tri-tert-butylphosphine)palladium

Single-step synthesis of styryl phosphonic acids: Via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides

We have developed a single step palladium-catalyzed Heck coupling of aryl halides with vinyl phosphonic acid to produce functionalized (E)-styryl phosphonic acids. This pathway utilizes a variety of commercially available aryl halides, vinyl phosphonic acid and Pd(P(tBu)3)2 as catalyst. These conditions produce a wide range of styryl phosphonic acids with high purities and good to excellent yields (31-80%).

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Recommanded Product: 53199-31-8, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 53199-31-8, name is Bis(tri-tert-butylphosphine)palladium. In an article，Which mentioned a new discovery about 53199-31-8

Asymmetric N-H Insertion of secondary and primary anilines under the catalysis of palladium and chiral guanidine derivatives

Efficient enantioselective N-H insertion reactions of secondary and primary anilines were catalyzed by palladium(0) in combination with chiral guanidine derivatives. A broad range of substituted anilines were tolerated, and the corresponding products were obtained in high yield (up to 99 %) with good enantioselectivity (up to 94 % ee) under mild reaction conditions. The N-H insertion mechanism was examined by the study of kinetic isotope effects, control experiments, HRMS, and spectroscopic analysis. Hidden talents: Chiral guanidine derivatives were developed as useful ligands for the enantioselective insertion of carbenoids into the N-H bonds of secondary and primary anilines in combination with palladium(0), which was not previously known to promote asymmetric N-H insertion (see scheme; dba=dibenzylideneacetone). The N-H insertion mechanism was examined by kinetic isotope studies, control experiments, HRMS, and spectroscopic analysis. Copyright

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Subtle balance of ligand steric effects in stille transmetalation

Experimental results have previously suggested that the transmetalation step in the Stille reaction is hindered at one extreme by very bulky ligands L on the PdL2 catalyst, yet at the other extreme, transmetalation is also found to be slow for small ligands. Our aim in this paper is to resolve this dilemma using computational chemistry and to show which ligand is best and why. With the use of density functional theory we show that the reason why L = PtBu3 retards transmetalation is because the bulky ligand hinders the coordination of the organostannane. On the other hand a small ligand such as L = PMe3 leads to the formation of a very stable intermediate in the catalytic cycle which then requires a large activation energy for the transmetalation to proceed. The L = PPh3 ligand appears to provide just the right balance in that it can readily coordinate the organostannane but avoids forming the very stable intermediate, and is thus the ligand of choice. L = PPh2Me is predicted to be the next best option, but L = PPhMe2 is too small and forms an intermediate whose stability prevents further reaction in the transmetalation step. Our calculations are also able to account for the accelerating role of CsF in the transmetalation step of the Stille reaction. Finally, this work demonstrates the importance of taking into account the steric properties of the full ligand in theoretical studies of such reactions, rather than using small model phosphines.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Compounds & Methods for the Enhanced Degradation of Targeted Proteins & Other Polypeptides by an E3 Ubiquitin Ligase

The present invention relates to bifunctional compounds, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins that are degraded and/or otherwise inhibited by bifunctional compounds of the present invention. In particular, the present invention is directed to compounds, which contain on one end a VHL ligand that binds to the ubiquitin ligase and on the other end a moiety that binds a target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. The present invention exhibits a broad range of pharmacological activities associated with compounds of the present invention, consistent with the degradation/inhibition of targeted polypeptides.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Synthetic Route of 53199-31-8, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 53199-31-8, molcular formula is C24H54P2Pd, introducing its new discovery.

Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: Efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp3-hybridized carbons

Pd0-mediated rapid cross coupling between sp3- hybridized carbons of CH3I and benzyl- or cinnamylboronic acid esters using [Pd{P(tert-C4H9)3}2]/CsF in DMF/H2O gave the corresponding methylated compounds in high yield. The utility was well demonstrated for the synthesis of short-lived PET tracer, N-(4-[11C]ethylphenyl)propionamide, in 90 ± 1% radio-HPLC analytical yield and 49 ± 3% radiochemical yield.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (PtBu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (tBu3P)(CO) Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Synthetic Route of 53199-31-8, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Patent, and a compound is mentioned, 53199-31-8, Bis(tri-tert-butylphosphine)palladium, introducing its new discovery.

PROCESS

The present invention provides a process for the preparation of a complex of formula (I): comprising the step of reacting Pd(diolefin)X2 or PdX2 and PR1 R2R3 in a solvent to form the complex of formula (I), wherein the process is carried out in the absence of a base, the molar ratio of Pd(diolefin)X2 : PR1 R2R3 or PdX2 : PR1 R2R3 is greater than 1 : 1.1, up to about 1 :2.5; each X is independently a halide; and R1, R2 and R3 are independently selected from the group consisting of tert-butyl and isopropyl.

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Reference：
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method