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Steric and Electronic Influences of Buchwald-Type Alkyl-JohnPhos Ligands

The electron-donating and steric properties of Buchwald-type ligands ([1,1?-biphenyl-2-yl]dialkylphosphine; R-JohnPhos, where R = Me, Et, iPr, Cy, tBu) were determined. The pi-acidity and sigma-donating properties of the R-JohnPhos ligands were quantified using a Cotton-Kraihanzel analysis of the Cr0(CO)5(R-JohnPhos) complexes. Somewhat surprisingly, the sigma-donating abilities of the R-JohnPhos ligands follow the trend tBu-JohnPhos < Et-JohnPhos < iPr-JohnPhos < Cy-JohnPhos ? Me-JohnPhos. This ordering is proposed to arise from competition between the intrinsic electron-donating ability of the R groups (Me < Et < iPr ? Cy < tBu) and steric interactions (front and back strain) that decrease the electron-donating ability of the phosphine. X-ray crystallographic data of 22 metal complexes (general forms: trans-Cr0(CO)4(PR3)2, Pd0(PR3)2(eta2-dba), and trans-PdII(Cl)2(PR3)2) were also analyzed to help explain the electronic trends measured for the R-JohnPhos ligands. The R-JohnPhos ligands are exceptionally sensitive to back strain in comparison to typical phosphines, and the strong sigma-donating ability of the Methyl-JohnPhos ligand is attributed to its ability to avoid both front strain and back strain. Consequently, the -PMe2 moiety allows for very short phosphorus-metal bond distances. Because of the sterically dominating o-biphenyl and close phosphorus-metal bond distances, MeJPhos maintains a large overall steric profile that is actually larger than that of CyJPhos as measured by percent buried volume (%Vbur). Overall, the -PMe2 moiety is a powerful way to incorporate strong sigma-donation into "designer" phosphines while retaining other advantageous structural and reactivity properties. One of the oldest and most widely used commercial enzyme inhibitors is aspirin, Safety of Tris(dibenzylideneacetone)dipalladium-chloroform, which selectively inhibits one of the enzymes involved in the synthesis of molecules that trigger inflammation. you can also check out more blogs about 52522-40-4

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

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Palladium-catalyzed enantioselective decarboxylative cycloaddition of vinylethylene carbonates with isocyanates

An efficient method for the enantioselective construction of beta-substituted beta-vinylglycinol derivatives through palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with isocyanates was developed. By using a palladium complex generated in situ from [Pd2(dba)3] ¡¤ CHCl3 (dba=dibenzylideneacetone) and (S)-Segphos as a catalyst under mild reaction conditions, the process provided 4-substituted-4-vinyloxazolidin-2-ones in high yields with a high level of enantioselectivity.The stereochemical outcome of the reaction was explained by DFT calculations and the synthetic utility of the process was demonstrated by the gram-scale transformation and formal synthesis of MK-0731 as a kinesin spindle protein inhibitor.

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

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Short Effective Synthesis of alpha-Fluoroketones by Palladium-Catalyzed Decarboxylation Reactions of Allyl alpha-Fluoro-beta-keto Carboxylates

alpha-Fluoroketones, alpha-fluoro-alpha-allylketones, and alpha-fluoro-alpha,beta-unsaturated ketones are synthesized by palladium-catalyzed decarboxylation reactions of allyl alpha-fluoro-beta-keto carboxylates.

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

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Ring expansion of a platinacyclopropane to a platinacyclopentane by double insertion of isocyanides into Pt-C bonds

A platinum isocyanide complex bearing a eta2-TCNE ligand, (eta2-TCNE)Pt(eta-CNC6H3-2,6-Me 2)2 (1), was synthesized, and its crystallographic study revealed the coordination mode of the eta2-TCNE ligand to be a typical metallacyclopropane extreme, in which back-donation from metal to TCNE contributes primarily to the stabilization of 1. Treatment of 1 with 2 equiv of CNC6H3-2,6-Me2 resulted in ring expansion of the platinacyclopropane by insertion of CNC6H3-2,6-Me 2 into each Pt-C bond of the metallacycle, leading to formation of a new complex having a platinacyclopentane structure, (TCNE)Pt(eta-CNC 6H3-2,6-Me2)4 (4). Although the molecular structures of palladium and nickel homologues of 1 were close to the corresponding metallacyclopropane, no metallacyclopentane complex was obtained under similar conditions. Studies on variable-temperature NMR spectroscopy and spin-saturation transfer measurement of 4 showed exchange of the imidoyl CNC6H3-2,6-Me2 group and the coordinated CNC6H3-2,6-Me2 ligand in solution, suggesting the ring expansion to be reversible.

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

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A catalytic asymmetric construction of a tetrahydroquinoline-based spirooxindole framework: Via a diastereo- and enantioselective decarboxylative [4+2] cycloaddition

A catalytic asymmetric decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with methyleneindolinones has been established, which provided a series of chiral tetrahydroquinoline-based 3,3?-spirooxindoles in high yields (up to 96%) and with excellent diastereo- and enantioselectivities (all >95:5 d.r., up to 99% ee). This reaction not only represents the first example of catalytic enantioselective [4+2] cycloaddition between methyleneindolinones and Pd-containing 1,4-dipoles, but also demonstrates the great practicability of catalytic asymmetric decarboxylative cycloadditions in the synthesis of enantio-enriched polycyclic compounds.

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

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Palladium(0)-Catalyzed Diastereoselective (3+2) Cycloadditions of Vinylcyclopropanes with Sulfonyl-Activated Imines

We report herein a palladium(0)-catalyzed (3+2)-cycloaddition process between vinylcyclopropanes and cyclic or acyclic sulfonylimines. This reaction, which operates under low catalyst loading and practical reaction conditions, gives access to a wide variety of N-heterocyclic derivatives in good to excellent yields and high levels of diastereoselectivity.

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

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Hydrophilic Pd0 complexes based on sugars for efficient Suzuki-Miyaura coupling in aqueous systems

Two classes of hydrophilic Pd0 complexes containing P,N and N,N sugar-based ligands were prepared and tested in the Suzuki-Miyaura cross-coupling reaction under environmentally friendly aqueous conditions. The best catalyst was tolerant towards different substrates, and its activity is comparable with the highest values reported so far for reactions in aqueous media [loading 0.0010 %, turnover frequency (TOF) 3.5 ¡Á 104 h-1].

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

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Synthesis of fused tetracyclic spiroindoles via palladium-catalysed cascade cyclisation

Efficient palladium-catalysed cascade cyclisation to form spiroindoles is developed. Treatment of indoles bearing a propargyl chloride side chain at the 3-position with various external nucleophiles in the presence of a catalytic amount of Pd2(dba)3¡¤CHCl3/dppb and Cs2CO3 in THF gives fused tetracyclic spiroindoles in moderate to good yields.

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

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Pd-Catalyzed Decarboxylative Asymmetric Protonation of Sterically Hindered alpha-Aryl Lactones and Dihydrocoumarins

Pd-catalyzed decarboxylative asymmetric protonation (DAP) has been developed for sterically hindered alpha-aryl lactone and dihydrocoumarin substrates. Optimization studies were conducted using delta-lactone- and dihydrocoumarin-derived alpha-aryl, beta-oxo-allyl esters with 2,4,6-trimethoxyphenyl as the aryl substituent. In the absence of a chiral P,N-ligand, (1R,2S)-(?)ephedrine, a cheap and readily available chiral proton donor, induced enantioselectivities of up to 92% ee and 88% ee with lactone and dihydrocoumarin substrates, respectively. Bulky aryl groups containing di-ortho substitutions and naphthyl groups gave the highest enantioselectivities of up to 92% and 86%, respectively. A stereochemical rationale is proposed to explain the preferred sense of asymmetric induction. (Figure presented.).

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

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Synthesis of tetra-pincer nickel(ii) and palladium(ii) complexes of resorcin[4]arene-octophosphinite [Res(OPR2)8] and rhodium-catalyzed regioselective hydroformylation reaction

The condensation reaction of resorcinol with pentanal yielded resorcin[4]arene 1 which on bromination using N-bromosuccinimide at room temperature produced tetra-bromide derivative 2. The reactions of 2 with chlorodiphenylphosphine and o-phenylenephosphoro-chloridite yielded octaphosphinite 3 (hereafter referred to as octaphos) and octaphosphite 4, respectively. The reactions of 3 with Ni(COD)2 or Pd2(dba)3¡¤CHCl3 in appropriate molar ratios yielded tetra-pincer complexes 5 and 6, respectively. The structures of both the complexes were established by single crystal X-ray diffraction studies. The resorcin[4]arene backbone adopts a boat structure in these complexes. Typically, the Rh-catalyzed hydroformylation of styrene prevalently delivers a branched (b) chiral aldehyde. A unique resorcin[4]arene skeleton based octaphos 3 was employed in the Rh-catalyzed hydroformylation of styrene. The hydroformylation of styrene with a metal to ligand ratio of 1:1 (M:L) was found to be regioselective, producing a linear (l) aldehyde as a major product with 100% conversion in 3 h. The l:b ratio surprisingly increased when the ortho positions of styrene were populated by methyl and chloro substituents. The hydroformylation of p-nitro styrene triggered a remarkably high linear:branched aldehyde ratio of 2.4 (71% linear aldehyde) despite its electron withdrawing nature. The highest linear selectivity of 97% (l:b ratio 27.8) was achieved in the case of 2,4,6-trimethylstyrene.

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