Tag: M.W:200-300

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Complexes of the type [{(dippe)Ni} ( 2-Calpha,Cbeta- 1,4-dien-3-one)] (dippe = 1,2-bis(diisopropylphosphino)- ethane); n= 1, 2; enone = aromatic 1,4-pentadien-3-ones) were synthesized. The “[(dippe)Ni]” moiety derived from [(dippe)Ni(-H)]2 2-coordinated to the C,C double bonds of the corresponding alpha,beta-unsaturated enone and was fully characterized using a variety of spectroscopic techniques, for instance, single-crystal X-ray diffraction, nuclear magnetic resonance (NMR), and mass spectrometry. The complexes were assessed in a catalytic transfer hydrogenation process using methanol (CH3OH) as a hydrogen donor. This alcohol turned out to be a very efficient reducing and alkylating agent of 1,4- pentadien-3-ones, under neat conditions. The current methodology allowed the selective reduction of C=C bonds in alpha,beta- unsaturated enones to yield enones and saturated ketones by a homogeneous catalytic pathway, whereas by a heterogeneous pathway, the process leads to the formation of mono- and dimethylated ketones. In the latter case, the occurrence of nickel nanoparticles in the reaction media was found to participate in the catalytic alkylation of such dienones.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A surprisingly stable homoleptic Pd04 chain complex of non-activated olefins was isolated and structurally characterized by X-ray crystallographic analysis, and the unique structure and bonding are compared to those of the corresponding dicationic [Pd4]2+ chain sandwich complex. The Royal Society of Chemistry.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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An exo-selective one-pot synthesis of novel spiro[cyclohexanone-pyrandione] derivatives through two sequential organobase-catalysed 1,4-conjugate additions of pyran-2,4-dione precursors on diarylideneacetone derivatives is described. The resulting 7,11-diaryl-2-oxaspiro[5.5]undec-3-ene-1,5,9-triones were obtained as a 2:1 mixture of exo- and endo-diastereomers and adopt a meso-form due to the bilateral symmetry existing in the scaffold. Chiral-HPLC, NMR and single-crystal X-ray diffraction (including synchrotron data) have been used to elucidate the spiro[cyclohexanone-pyrandione] structure, showing therefore the exo/endo-diastereomers obtained in a meso-form, the cis-7,11-diaryl configuration (equatorial position) and different conformational changes in the cyclohexanone skeleton both in liquid and solid states. DFT studies proved the exo-stereoselectivity of the reaction by determining the exo/cis equatorial-equatorial configuration as the most thermodynamically stable form of our spiro[cyclohexanone-pyrandione] skeleton, while the structural substitution has no effect.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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We report on the synthesis of a variety of C,E-bidentate triazolylidene ruthenium complexes that comprise different donor substituents E (E = C: phenyl anion; E = O: carboxylate, alkoxide; E = N: pyridine at heterocyclic carbon or nitrogen). Introduction of these donor functionalities is greatly facilitated by the synthetic versatility of triazoles, and their facile preparation routes. Five different complexes featuring a C,E-coordinated ruthenium center with chloride/cymene spectator ligands and three analogous solvento complexes with MeCN spectator ligands were prepared and evaluated as catalyst precursors for direct base- and oxidant-free alcohol dehydrogenation, and for transfer hydrogenation using basic iPrOH as a source of dihydrogen. In both catalytic reactions, the neutral/mono-cationic complexes with chloride/cymene spectator ligands performed better than the solvento ruthenium complexes. The donor functionality had a further profound impact on catalytic activity. For alcohol dehydrogenation, the C,C-bidentate phenyl-triazolylidene ligand induced highest conversions, while carboxylate or pyridine donor sites gave only moderate activity or none at all. In contrast, transfer hydrogenation is most efficient when a pyridyl donor group is linked to the triazolylidene via the heterocyclic carbon atom, providing turnover frequencies as high as 1400 h-1 for cyclohexanone transfer hydrogenation. The role of the donor group is discussed in mechanistic terms.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The (+)-sparteine-mediated lithiation-substitution of o-benzyl-N- pivaloylaniline with various ketones was investigated. The obtained highly enantioenriched tertiary alcohols were used for the synthesis of alkenyl-substituted products 12 and 13 as well as 3,3,4-trisubstituted tetrahydroquinoline derivatives 22-24. The reaction with alpha,beta- unsaturated ketones afforded highly enantioenriched 1,4-addition products 28-33 and provided a protocol for the asymmetric synthesis of highly substituted tetralin derivative 34. Copyright

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize beta-aryl alpha,beta-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A novel and efficient method has been developed for the chemoselective conjugate reduction of alpha,beta-unsaturated ketones with tosylhydrazine as a hydrogen source to the corresponding saturated ketones in moderate to good yields. The present protocol does not require the use of transition metal, and is efficient being applicable to a wide range of substrates (25 examples).

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The reaction of 4,5-diamino-3-methyl-1-phenylpyrazole with dibenzylideneacetone and its 4,4′-derivatives has been studied; the reactions lead to aromatic 1H-2,3-dihydropyrazolo<5,4-b>-1,5-diazepine derivatives.The reaction pathway has also been identified.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Cetyltrimethylammonium peroxodisulfate (CTA)2S2O 8 was quantitatively prepared and used for the deprotection of oximes, phenylhydrazones, semicarbazones and thiosemicarbazones to the corresponding carbonyl compounds in acetonitrile. Its agent is more efficient and has advantages over similar reagents in terms of the amount of oxidant, short reaction time, simple work up, and high yield.

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A highly water dispersible Pd-aminoclay nanocomposite is found to be effective catalytic system for the hydrogenation of alpha,beta-unsaturated carbonyl compounds and Suzuki coupling reactions in aqueous media. The catalytic hydrogenation of alpha,beta-unsaturated carbonyl compounds proceeds at room temperature to afford the corresponding products in excellent yields with high chemoselectivity. The cross coupling of aryl bromides and iodides with aryl boronic acids proceeds efficiently under aqueous conditions at 90 C to afford the corresponding biaryls in excellent yields with high selectivity. The Suzuki reaction proceeds smoothly even in the absence of external base due to the basic nature of the catalyst support. The catalyst could be easily recovered and recycled three times without a significant loss of activity in hydrogenation and Suzuki cross coupling reactions. Copyright

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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate