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Thiazole-containing pi-conjugated moieties are important structural units in the development of new electronic and photochromic materials. We have developed a Pd-catalyzed syn-hydroarylation reaction of diaryl alkynes with thiazoles that provides access to thiazole-containing triarylethylenes. Pd(II) complexes derived from Pd(0) species and carboxylic acids facilitated C-H functionalization of the unsubstituted thiazole with high C5 selectivity. The catalytic system was also compatible with other azoles, such as oxazoles and a pyrazole, allowing the stereoselective syntheses of various trisubstituted olefins.

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

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Several new neutral and cationic organopalladium complexes containing a P-N chelating ligand, 2-(diisopropylphosphinomethyl)-1-methylimidazole, have been synthesized and characterized. The neutral complexes [PdPh(I)(P-N)] 1 and [PdMe(I)(P-N)] 2 have been synthesized by oxidative addition of PhI and MeI, respectively to Pd(dba)2 (dba = dibenzylideneacetone) in the presence of the P-N ligand. The cationic complexes [PdPh(PPh3)(P-N)]BF4 3 and [PdMe(PPh3)(P-N)]BF4 4 were obtained by adding an acetone solution of AgBF4/PPh3 to the corresponding neutral precursors 1 and 2, respectively. A cationic allyl complex, [Pd(eta3-C3H5)(P-N)]Br 5, has also been prepared by oxidative addition of 3-bromopropene to Pd(dba)2 in presence of the P-N ligand. Single crystal structure determinations have been carried out for 1, 4 and 5. Carbonylation of the metal-carbon bond in these new complexes was also studied. The neutral complexes 1 and 2 react smoothly with CO to give carbonylated products [Pd(C(O)Ph)I(P-N)] 6 and [Pd(C(O)Me)I(P-N)] 7, respectively. The methyl complex 2 reacted much faster than the phenyl complex 1. The cationic complexes 3 and 4 are inert and do not give any carbonylated product. However, in the case of the reaction of 3, evidence has been obtained for the formation of a CO-coordinated complex [PdPh(PPh3)(CO)(P-N)]BF4 8 in which the P-N ligand temporarily acts as a monodentate phosphorus-bonded ligand. On the other hand, a cationic complex containing a weakly coordinating acetone molecule, [PdMe{(CD3)2CO}(P-N)]BF4 9, showed an enhanced reactivity toward CO and gave [Pd{MeC(O)}(CO)(P-N)]BF4 10.

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

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Four three-coordinate arylpalladium amido complexes with a single hindered phosphine were isolated and structurally characterized. Each possessed a T-shaped geometry. Several of these complexes possessed true three-coordinate structures that lacked any additional coordination by ligand C-H bonds. All of the three-coordinate complexes underwent reductive elimination to form the corresponding triarylamine. A comparison of the rate of reaction of the three-coordinate compounds demonstrated that the rate of elimination from the pentaphenylferrocenyl di-tert-butylphosphine complex were the fastest. A comparison of the rates of reactions between three-coordinate and four-coordinate complexes showed that the rates were much faster from the three-coordinate complexes. 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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The present invention relates to a method of carrying out an organic reaction in aqueous solution in the presence of a hydroxyalkyl(alkyl)cellulose or an alkylcellulose.

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Reference:
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Palladium/carbon catalyst regeneration and mechanical application method

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We have previously shown that hydroxyethylamines can be potent inhibitors of the BACE1 enzyme and that the generation of BACE1 inhibitors with CYP 3A4 inhibitory activities in this scaffold affords compounds (e.g., 1) with sufficient bioavailability and pharmacokinetic profiles to reduce central amyloid-beta peptide (Abeta) levels in wild-type rats following oral dosing. In this article, we describe further modifications of the P1-phenyl ring of the hydroxyethylamine series to afford potent, dual BACE1/CYP 3A4 inhibitors which demonstrate improved penetration into the CNS. Several of these compounds caused robust reduction of Abeta levels in rat CSF and brain following oral dosing, and compound 37 exhibited an improved cardiovascular safety profile relative to 1.

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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 first arylpalladium(IV) complexes, (bpy = 2,2′-bipyridyl), have been isolated upon oxidative addition of methyl iodide or benzyl bromide to .These dialkyl(aryl)palladium(IV) complexes undergo reductive elimination in solution at ca. 0 deg C: decomposes quantitatively into and toluene whereas gives ethane and toluene in 4:1 ratio together with the corresponding complexes (R = Me or Ph).The reaction of methyl iodide with at 0 deg C yields ethane and without detection of a palladium(IV) intermediate.No reaction of with benzyl bromide was observed.The first demonstration that organic groups can be transferred from palladium(IV) to palladium(II) is reported.The molecular of in the solid state has been determined.

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

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Treatment of [3]ferrocenophane (1) with 0.7 eq. or 3 eq. of BBr3 in hexane at reflux temperature gives the corresponding dibromoboryl (2) or 1,1?-bis(dibromoboryl) derivative (3) in good yields. Compounds 2 and 3 can be transformed into the corresponding di(tert-butoxy)boryl (4, 5) and pinacolboryl [3]ferrocenophanes (6, 7). Reaction of 6 and 7 with aqueous CuBr2 in MeOH/iPrOH at reflux temperature leads to the formation of the mono-and 1,1?-di-brominated [3]ferrocenophanes 8 and 9; subsequent Stilletype CeC-coupling reactions with nBu3SnPh yield mono-and 1,1?-di-phenylated [3]ferrocenophanes. Treatment of 6 with Li[AlH 4] in Et2 O at -78C provides access to the monotopic lithium trihydridoborate 12.

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

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Complexes of Pd(tcne) (tcne = tetracyanoethylene) containing bidentate ligands with large bite angles, bis<2-(diphenylphosphino)phenyl> ether (L1), 4,6-bis(diphenylphosphino)-10,10-dimethyl-10H-dibenzo<1,4>oxasiline (L2), 4,5-bis(diphenylphosphino)-2,8-dimethylphenoxathiine (L3), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (L4) and trans-5,6-bis(2-pyridyl)bicyclo<2.2.1>hept-2-ene (L6), were prepared and characterised.The compound 4,6-bis(diphenylphosphino)dibenzofuran (L5) did not form chelating palladium complexes, owing to its large natural bite angle of 138 degree.The crystal structures of L6, *2.5CH2Cl2 1, *4CH2Cl2 2, *2CH2Cl2 4 and 5 have been determined.The similarity of electronic effects induced by the free diphosphines was demonstrated by MOPAC calculations.The geometries of the ligands, however, were most accurately predicted by molecular mechanics (MM2) calculations for the diphosphines, and MNDO for L6.The largest P-Pd-P angle in the zerovalent palladium complexes was found to be 104.6 degree.A further increase in the natural bite angle of the ligand results in elongation of the Pd-P bond length in the complex rather than enlargement of the P-Pd-P bite angle.The ligand L6 assumed a bite angle of 99.5(2) degree in complex 5, which is considerably smaller than its calculated value of 117 degree.

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

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PROBLEM TO BE SOLVED: To raise the activity of polymerization catalyst in the copolymerization of alpha-olefin with a polar group-containing monomer, especially the copolymerization with a (meth)acrylic acid-based monomer.

SOLUTION: New triarylphosphine and triarylarsine compounds, each having a specific structure, are made to be a catalyst of the copolymerization of alpha-olefin with a polar group-containing monomer, by using a metal complex as a ligand in a catalyst composition. By the copolymerization catalyst with high catalytic activity, the industrialization of the copolymerization of alpha-olefin with a (meth)acrylic acid-based olefin is attained, the olefin copolymer thus obtained excels in mechanical and thermal physical properties, and is applicable as various kinds of useful molded products.

COPYRIGHT: (C)2010,JPO&INPIT

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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 compound Pd(eta3-1-Ph-C3H4) (eta5-C5H5) (I) reacts cleanly with many tertiary phosphines L to undergo reductive elimination of PhC3H 4-C5H5 and form palladium(0) species of the types PdLn (n = 2, 3), long believed to be exemplary catalysts for Suzuki-Miyaura, Heck-Mizoroki, and Sonogashira cross-coupling reactions. I has accordingly been shown to be generally much more effective for these catalytic processes than are conventional catalyst precursors such as Pd(PPh 3)4, Pd2(dba)3, PdCl2, and Pd(OAc)2, in large part because I stands alone in this series for its ability to generate specifically and efficiently the desired species PdL2 in many cases. We have now investigated I as a precursor for prototypical Buchwald-Hartwig amination reactions of 4-bromo- and 4-chloroanisole with morpholine, making comparisons with Pd2(dba) 3, Pd(OAc)2, and [Pd(eta3-1-Ph-C 3H4)Cl]2 (IV). In this work we have utilized PBut3 because of its general effectiveness, and we have also assessed XPhos and Mor-Dalphos, representatives of important classes of phosphines utilized elsewhere for amination reactions.

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