Discovery of Tris(dibenzylideneacetone)dipalladium-chloroform

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A difluorodienophile, synthesised using a Stille coupling reaction underwent tin(iv)-catalysed cycloaddition with three furans to afford oxa[2.2.1]bicycloheptenes in good yield. Reduction of ester and carbamate carbonyl groups and diol protection as the acetonide set the stage for palladium-catalysed hydrostannylation in two cases. Treatment of the stannanes with methyllithium triggered ring-opening to afford highly-functionalised difluorinated cyclohexenols which could be deprotected to afford (hydroxymethyl)conduritol analogues.

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

Archives for Chemistry Experiments of Bis(dibenzylideneacetone)palladium

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The asymmetric allylic alkylation (AAA), which features employing active allylic substrates, has historical significance in organic synthesis. The allylic C-H alkylation is principally more atom- and step-economic than the classical allylic functionalizations and thus can be considered a transformative variant. However, asymmetric allylic C-H alkylation reactions are still scarce and yet underdeveloped. Herein, we have found that Z/E- and regioselectivities in the Pd-catalyzed asymmetric allylic C-H alkylation of 1,4-dienes are highly dependent on the type of nucleophiles. A highly stereoselective allylic C-H alkylation of 1,4-dienes with azlactones has been established by palladium-chiral phosphoramidite catalysis. The protocol proceeds under mild conditions and can accommodate a wide scope of substrates, delivering structurally divergent alpha,alpha-disubstituted alpha-amino acid surrogates in high yields and excellent levels of diastereo-, Z/E-, regio-, and enantioselectivities. Notably, this method provides key chiral intermediates for an efficient synthesis of lepadiformine marine alkaloids. Experimental and computational studies on the reaction mechanism suggest a novel concerted proton and two-electron transfer process for the allylic C-H cleavage and reveal that the Z/E- and regioselectivities are governed by the geometry and coordination pattern of nucleophiles.

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

Archives for Chemistry Experiments of 52409-22-0

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The Pd-benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji-Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.

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

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A straightforward route toward construction of alpha-quaternary chiral beta-lactam moiety via Rh(II)/Pd(0)-catalyzed stereoselective relay catalytic reaction is reported. This asymmetric dual relay catalysis involves Rh(II)-catalyzed enantioselective intramoluecular C-H insertions of alpha-diazoamides, and sequential Pd(0)-catalyzed diastereoselective intermolecular allylic alkylation. Under mild reaction conditions, a broad range of alpha-quaternary allylated chiral beta-lactams have been synthesized in high yields (up to 99%) with excellent stereoselectivities [up to diastereomeric ratio (dr) >99:1, up to 98% enantiomeric excess (ee)].

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

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Oxovanadium(IV) immobilized on Fe3O4@S-ABEN is reported as a highly efficient nanocatalyst for the oxidation of sulfides and oxidative coupling of thiols (using H2O2 as green oxidant), the products of which are obtained in high to excellent yields. The products can be separated by a simple extraction with organic solvent and the catalyst is highly efficient, especially in terms of selectivity of desired product. The catalytic system can be recycled and reused without significant loss of catalytic activity.

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

The important role of Pd2(DBA)3

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The present invention provides transition-metal-catalyst-based methods for the arylation and vinylation of activated methyl, methylene, and methine carbons with aryl halides, vinyl halides, and the like. The methods of the invention provide several improvements over existing methods, including the ability to synthesize efficiently and under mild conditions alpha-aryl and alpha-vinyl products from a wide range of starting materials, including ketones, esters, hydrazones, and imines. Furthermore, the methods of the invention may be used in an asymmetric sense, i.e. to produce enantiomerically-enriched chiral alpha-aryl and alpha-vinyl products.

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

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A novel and direct synthesis of various 2-aminobenzo[b]thiophenes has been developed. The reactions were catalyzed by a combination of Pd(dppf)Cl2 and dppf using odorless and cheap Na2S2O3 as the sulfur source. This strategy allowed us to synthesize important 2-aminobenzo[b]thiophene scaffold more efficiently and conveniently.

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

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A signalling molecularly imprinted polymer was synthesised for easy detection of tamoxifen and its metabolites. 6-Vinylcoumarin-4-carboxylic acid (VCC) was synthesised from 4-bromophenol to give a fluorescent monomer, designed to switch off upon binding of tamoxifen. Clomiphene, a chlorinated analogue, was used as the template for the imprinting, and its ability to quench the coumarin fluorescence when used in a 1:1 ratio was demonstrated. Tamoxifen and 4-hydroxytamoxifen were also shown to quench coumarin fluorescence. Imprinted and non-imprinted polymers were synthesised using VCC, methacrylic acid as a backbone monomer and ethylene glycol dimethacrylate as cross-linker, and were ground and sieved to particle sizes ranging between 45 and 25 mum. Rebinding experiments demonstrate that the imprinted polymer shows very strong affinity for both clomiphene and tamoxifen, while the non-imprinted polymer shows negligible rebinding. The fluorescence of the imprinted polymer is quenched by clomiphene, tamoxifen and 4-hydroxytamoxifen. The switch off in fluorescence of the imprinted polymer under these conditions could also be detected under a UV lamp with the naked eye, making this matrix suitable for applications when coupled with a sample preparation system.

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

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How molecular conformation variation due to the existence of steric torsions within the conjugated backbones plays a role in molecular packing and resultant polymer solar cell (PSC) performance was investigated by synthesizing two isomeric alternating D-A copolymers. In these copolymers, poly{3?,4?-dihexyl-(2,2?:5?,2??-terthiophene)-5,5??-diyl-alt-[4?,7?-di-2-(4-(2?-ethylhexyl))thienyl-(5?,6?-difluorobenzo[c][1?,2?,5?]thiadiazole)]-5,5-diyl} (PTDTffBT(C6/EH)) and poly{3?,4?-di(2?-ethylhexyl)-(2,2?:5?,2??-terthiophene)-5,5??-diyl-alt-[4?,7?-di-2-(4-hexyl) thienyl-(5?,6?-difluorobenzo[c][1?,2?,5?]thiadiazole)]-5,5-diyl} (PTDTffBT(EH/C6)), which had comparable molecular weight, the linear hexyl and branched 2-ethylhexyl chains are interchanged between the donor and the acceptor units. Such molecular design could offer two isomeric donors with limited conformational steric distortions by positioning the given alkyl chains with fine steric disparity in the same conjugated backbone. The interchange of the side chains caused a fluctuation of ?5 of the dihedral angles between the thiophenes within the donor units and between the ending thiophenes from the adjacent donor and acceptor units. The subtle transform on backbone steric distortions of the two copolymers leads to a negligible impact on electronic structures but a distinct one on molecular packing in film. The copolymers both embody polymorph molecular packing with preferential edge-on orientation in neat films. The (100) and (010) distance, corresponding to the lamellar stacking between the alkyl chains and the pi-pi stacking between the conjugated backbones, are both improved in the PTDTffBT(C6/EH) film with enhanced crystallinity than that in the PEDTffBT(EH/C6) film. Similar molecular packing feature remains for the BHJ blends of the two copolymers with the acceptor of PC71BM. Moreover, PTDTffBT(C6/EH) exhibits the apparant coexistence of face-on orientation with improved crystallinity. The PTDTffBT(C6/EH): PC71BM PSC devices offer a much improved maximum power conversion efficiency (PCE) of 8.24% over 6.13% of the PTDTffBT(EH/C6) device, mainly due to more efficient charge generation and balanced charge transport resulted from the optimized film microstructure. The investigation clearly shows the sensitivity of molecular packing and corresponding PSC device performance to subtle steric distortions within conjugated backbones.

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

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Enantioselective Pd(0)-catalyzed C-H functionalizations of ketene aminal phosphates provide isoindoline scaffolds with high enantioselectivity at ambient temperature. The high level of enantiocontrol is enabled by a tailored monodentate electron-rich phosphine ligand featuring a point-chiral phospholane module and a bulky atropchiral binaphthyl backbone.

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