Extracurricular laboratory:new discovery of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.

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

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The neopentyl ester of 1,3-di(2-pyridyl)benzene-5-boronic acid (dpy-B) is a useful intermediate in the divergent synthesis of N^C^N-coordinating, 1,3-di(2-pyridyl)benzene ligands, HLn, that carry aryl substituents at the 5-position of the central ring. The platinum(ii) complexes, PtL nCl, of several such ligands have been prepared, incorporating pendant anisoles, arylamines, an oxacrown, and an azacrown, all of which are strongly luminescent in solution at 298 K. The emission of the complexes is partially quenched by oxygen, and all of the compounds are very efficient sensitisers of singlet oxygen. The quantum yields of 1O2 formation have been measured on the basis of the intensity of the O 21Deltag emission at 1270 nm, and are in the range 0.25-0.65. Density functional theory (DFT) calculations have been carried out that include the effect of the solvent, on the unsubstituted complex PtL1Cl and on the derivatives incorporating p-dimethylaminophenyl and phenyl-15-mono-N-azacrown-5 pendants (PtL9Cl and PtL12Cl respectively). Absorption spectra have been simulated on the basis of the calculated singlet excitations: they closely resemble the experimental spectra. In particular, the DFT successfully accounts for the appearance of low-energy absorption bands that accompany the introduction of the aryl pendants, indicating the participation of the aryl group in the HOMO but not significantly in the LUMO. The calculated lowest energy triplet excitation of PtL 1Cl is close to the observed 0-0 emission maximum of this complex in solution. Taking together data for this series of complexes and related compounds previously studied, the energies of the lowest-energy spin-allowed absorption bands are shown to correlate approximately linearly with the oxidation peak potential. The emission energies show a similar correlation in toluene, but in CH2Cl2 the value for PtL9Cl is anomalously low. The differing emission properties of this complex in the two solvents suggest a switch to a TICT-like state in CH2Cl2 (TICT = twisted intramolecular charge transfer), stabilised in the more polar environment. Transient DC photoconductivity measurements confirm that the dipole moment of the triplet excited state is larger in CH2Cl2 than in toluene. The azacrown PtL12Cl displays similar behaviour. Binding of metal ions such as Ca2+ to the azacrown unit of this complex leads to a pronounced blue shift in the emission, which can be readily understood in terms of the large increase in the TICT energy that will accompany the binding of the metal ion to the lone pair of the azacrown nitrogen atom.

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

More research is needed about [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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ortho-Arylthio triarylbismuthanes [2-(Ar?S)C6H 4]nBiAr3-n have been conveniently synthesized by insertion of benzyne into the bismuth-sulfur bond of (Ar?S) nBiAr3-n (n = 1, 2). A similar insertion takes place when a homologous antimony congener is used, but no reaction is observed with its phosphorus analogue. This suggests a clear difference in the bond strength between pnictogen-sulfur bonds. The carbon-bismuth bond of [2-(2-BrC 6H4S)C6H4]nBiAr 3-n undergoes Pd-catalyzed intramolecular cross-coupling to produce dibenzothiophene in good yield. An X-ray crystallographic study of 2-(2-BrC 6H4S)C6H4BiTol2 (Tol = 4-MeC6H4) reveals that this molecule is present in a dimeric structure, where the six heteroatoms including bismuth, sulfur, and bromine are linked through the nonbonded intramolecular bismuth-sulfur and intermolecular sulfur-bromine and bromine-bromine interactions.

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

Some scientific research about Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II)

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A series of 8-heteroaryl substituted quinolines were prepared, either by direct C-H arylation of five-membered heteroarenes, or Pd-catalyzed coupling of organoboron reagents with bromoquinolines. The use of (benzo)thiophenyl or (benzo)furanyl boron coupling partners allowed further C-H functionalization on the five-membered heteroaryl ring with aryl bromides in one flask to access a variety of polyconjugated molecular architectures. The developed methodology represents a simple approach towards 8-arylated analogues of the biologically interesting nitroxoline core.

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

The Absolute Best Science Experiment for Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)

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The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.

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

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The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C?H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.

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

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Cyclometallated iridium complexes comprised of two terdentate cyclometallating ligands, of the form [Ir(NCN)(NNC)]+, have been explored for the preparation of multimetallic systems by palladium-catalysed cross-coupling reactions. An NNC-coordinating ligand carrying a boronate ester group has been prepared and complexed to iridium to give a boronic acid appended complex of this type, 3. This complex has been subjected to cross-coupling with a bromo-substituted bis-terpyridyl iridium complex to give a dinuclear iridium compound 6, in which one of the two iridium centres is N6-coordinated and the other has an N4C2-coordination sphere. Meanwhile, a bromo-substituted complex 4 has been coupled with a boronic acid-appended ruthenium complex, to give a dinuclear heterometallic complex 8 that can be activated to a second coupling by in situ bromination, offering access to a linear Ir-Ir-Ru trimetallic assembly 11. The electrochemical and luminescence properties of these systems are investigated. In the case of 8 and 11, the behaviour can be rationalised in terms of a supramolecular description: efficient energy transfer occurs from the Ir terminus to the Ru. In contrast, for compound 6, an excited state with significant bridge character appears to play a key role in determining the emission properties. The Royal Society of Chemistry 2009.

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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(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)

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The invention discloses two chlorine two uncles butyl – 4 – dimethyl amino […] preparation method, comprises the following steps: step 1, using raw materials N, N – dimethyl skating aniline and splicing preparation Grignard reagent; step 2, takes standard reagent and the temperature, and then adding the catalyst after-reaction, then dropwise di-tert-butyl chloride, to obtain the temperature of the after-reaction of di-tert-butyl – 4 – dimethyl amino phosphonate; step 3, to the di-tert-butyl – 4 – dimethyl amino phosphonate purification processing; step 4, taking double-(acetonitrile) palladium dichloride with purified di-tert-butyl – 4 – dimethyl amino phosphonate to the complexation reaction, to obtain the target product. The preparation method of the present invention to di-tert-butyl – 4 – dimethyl amino phosphonate to carry out purification process, high purity of di-tert-butyl – 4 – dimethyl amino phosphonate with double-(acetonitrile) palladium dichloride reaction, thereby greatly reducing the noble metal palladium yield losses, the preparation cost is greatly reduced, there is very good practical value. (by machine translation)

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

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The application of sterically hindered palladium catalysts to the regioselective hydrodebromination of 2,3,5-tribromothiophene has been studied in detail, including the effects of catalyst choice, solvent, reaction time, and temperature, as well as the method of NaBH4 addition and the role of chelating additives to effect NaBH4 solubility. Ultimately it was determined that the background reaction between NaBH4 and bromothiophenes is too facile to allow both total conversion and high selectivity. Optimized conditions finally allowed a selectivity of ca. 16:1 with overall conversion of 100%. However, complications of overdebromination under these conditions still limit the yield of the desired 2,3-dibromothiophene to 65%.

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

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The electronic spectrum of Pd0[(PPh2C5H4)2Fen]2 in CCl4 shows an absorption at lambdamax = 338 nm that is assigned to a charge transfer-to-solvent (CTTS) transition from the ferrocene moiety to CCl4. The CTTS excitation leads to the formation of PdII[(PPh2C5H4)2Fe II]Cl2. It is suggested that the irradiation induces initially the generation of FeIII, which then oxidizes Pd0 by intramolecular electron transfer. Product formation takes place by a disproportionation of PdI.

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