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A set of bench-stable ruthenium complexes with new N,N,N-tridentate coordinating pincer-type pyridyl-bis(pyridylideneamide) ligands was synthesized in excellent yields, with the pyridylidene amide in meta or in para position (m-PYA and p-PYA, respectively). While complex [Ru(p-PYA)(MeCN)3]2+ is catalytically silent in transfer hydrogenation, its meta isomer [Ru(m-PYA)(MeCN)3]2+ shows considerable activity with turnover frequencies at 50% conversion TOF50 = 100 h-1. Spectroscopic, electrochemical, and crystallographic analyses suggest considerably stronger donor properties of the zwitterionic m-PYA ligand compared to the partially pi-acidic p-PYA analogue, imparted by valence isomerization. Further catalyst optimization was achieved by exchanging the ancillary MeCN ligands with imines (4-picoline), amines (ethylenediamine), and phosphines (PPh3, dppm, dppe). The most active catalyst was comprised of the m-PYA pincer ligand and PPh3, complex [Ru(m-PYA)(PPh3)(MeCN)2]2+, which reached a TOF50 of 430 h-1 under aerobic conditions and up to 4000 h-1 in the absence of oxygen. The presence of oxygen reversibly deactivates the catalytically active species, which compromises activity, but not longevity of the catalyst. Ligand exchange kinetic studies by NMR spectroscopy indicate that the strong trans effect of the phosphine is critical for high catalyst activity. Diaryl, aryl-alkyl, and dialkyl ketones were hydrogenated with high conversion, and alpha,beta-unsaturated ketones produced selectively the saturated ketone as the only product due to exclusive C=C bond hydrogenation, a distinctly different selectivity from most other transfer hydrogenation catalysts.

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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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Masked silylene complexes Cp?(IXy-H)(H)RuSiH2R (R = Mes (3) and Trip (4); IXy = 1,3-bis(2,6-dimethylphenyl)imidazol-2-ylidene; “IXy-H” is the deprotonated form of IXy) exhibit metallosilylene-like (LnM-Si-R) reactivity, as observed in reactions of nonenolizable ketones, enones, and tosyl azides, to give unprecedented silaoxiranyl, oxasilacyclopentenyl, and silaiminyl complexes, respectively. Notably, these silicon-containing complexes are derived from the primary silanes MesSiH3 and TripSiH3 via activation of all three Si-H bonds. DFT calculations suggest that the mechanism of formation for the silaoxiranyl complex Cp?(IXy)(H)2Ru-Si(OCPh2)Trip (6) involves coordination of benzophenone to a silylene silicon atom, followed by a single-electron transfer in which Si-bonded, non-innocent benzophenone accepts an electron from the reactive, electron-rich ruthenium center. Importantly, this electron transfer promotes an unusual 1,2-hydrogen migration to the resulting, more electron-deficient ruthenium center via a diradicaloid transition state.

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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 high yielding, eco-friendly and simple procedure for the synthesis of five membered carbo- and heterocycles through cellulose sulfonic acid (CSA) mediated electrocyclization processes has been developed. Cellulose sulfonic acid (CSA) not only was able to induce the cyclization of “unactivated” dienones generating cyclopentenoids; it was also able to trigger the cyclization of alpha,beta-unsaturated hydrazones giving rise to pyrazolines in excellent yields under green reaction conditions. The ease of catalyst recovery and reusability, short reaction time, simple experimental and work-up procedure; compared to the conventional methods, makes this protocol practical, environmentally friendly and economically desirable. The cellulose-SO3H (CSA) was characterized by FT-IR spectroscopy, powder X-ray diffraction (XRD) and Scanning Electron Microscopy (SEM) analyses, and catalyst stability was judged by thermogravimetry/differential thermal analysis (TG/DTA). The catalyst can be recycled several times without significant loss of catalytic activity.

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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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N-Acetonylazoles react with chalcones in the presence of a base to give trans-3,5-disubstituted 6-(N-azolyl)cyclohex-2-enones. Usually, the reactions are fast and high-yielding.

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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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(S)-2-Methyloxetane (1) and its precursor (S)-1,3-butanediol (2) were prepared in low to moderate chemical yield with less than 0.5percent racemization from (S)-ethyl lactate (4) and from (2S,3S)-allothreonine (14b).For the first time the enantiomeric purities of both the starting material and the product (1) were carefully determined by high-precision capillary gas chromatography on optically active resolving stationary phases.The validity of the quadrant rule, correlating the relative configuration of alkyloxiranes with the order of elution from manganese(II) bis<(1R)-3-(heptafluorobutyryl)camphorate> (3) by complexation gas chromatography, is also confirmed for 2-methyloxetane (1).

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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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Chirality arising from isotope substitution, especially with atoms heavier than the hydrogen isotopes, is usually not considered a source of chirality in a chemical reaction. An N2,N2,N3,N3-tetramethyl-2,3-butanediamine containing nitrogen (14N/15N) isotope chirality was synthesized and it was revealed that this isotopically chiral diamine compound acts as a chiral initiator for asymmetric autocatalysis.

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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 cationic alkynyl Heck reaction between aryl triflates and alkynes to give substituted allenes is described. Key to the success of this method was the discovery and development of a new hybrid Pd(0)-catalyst, BobCat, that incorporates a water-soluble dba-ligand and biaryl phosphine ligand to provide substituted allenes in good yields under mild reaction conditions.

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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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Previously it has been shown that glycerol can be regioselectively glucosylated by sucrose phosphorylase from Leuconostoc mesenteroides to form 2-O-alpha-d-glucopyranosyl-glycerol (Goedl et al., Angew. Chem. Int. Ed. 47 (2008) 10086-10089). A series of compounds related to glycerol were investigated by us to determine the scope of the alpha-glucosylation reaction of sucrose phosphorylase. Both sucrose and glucose 1-phosphate (G1P) were applied as glucosyl donor. Mono-alcohols were not accepted as substrates but several 1,2-diols were readily glucosylated, proving that the vicinal diol unit is crucial for activity. The smallest substrate that was accepted for glucosylation appeared to be ethylene glycol, which was converted to the monoglucoside for 69%. Using high acceptor and donor concentrations (up to 2.5 M), sucrose or G1P hydrolysis (with H2O being the ‘acceptor’) can be minimised. In the study cited above, a preference for glucosylation of glycerol on the 2-position has been observed. For 1,2-propanediol however, the regiochemistry appeared to be dependent on the configuration of the substrate. The (R)-enantiomer was preferentialy glucosylated on its 1-position (ratio 2.5:1), whereas the 2-glucoside is the major product for (S)-1,2-propanediol (1:4.1). d.e. ps of 71-83% were observed with a preference for the (S)-enantiomer of the glucosides of 1,2-propanediol and 1,2-butanediol and the (R)-enantiomer of the glucoside of 3-methoxy-1,2-propanediol. This is the first example of stereoselective glucosylation of a non-natural substrate by sucrose phosphorylase. 3-Amino-1,2-propanediol, 3-chloro-1,2-propanediol, 1-thioglycerol and glyceraldehyde were not accepted as substrates. Generally, the glucoside yield is higher when sucrose is used as a donor rather than G1P, due to the fact that the released phosphate is a stronger inhibitor of the enzyme (in case of G1P) than the released fructose (in case of sucrose). Essentially the same results are obtained with sucrose phosphorylase from Bifidobacterium adolescentis.

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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 set of bioinspired carbamoyl CNP pincer complexes are reported that are relevant to [Fe]-hydrogenase (Hmd). The dicarbonyl species [(CNHNNHPR2)Fe(CO)2I] [R = Ph, 1; R = iPr, 2] undergoes ligand deprotonation, resulting in the dearomatized complexes of formulas [(CNHNN=PR2)Fe(CO)2] (5 and 6). The crystal structure and 1H{31P} NMR spectroscopy of the iodide-bound dearomatized species [Na(18-crown-6)][(CNHNN=PPh2)Fe(CO)2I] (7) showed that the deprotonated moiety was the phosphoramine N(H) linkage. Separately, the monocarbonyl complexes [(CNHNNHPR2)Fe(CO)(MeCN)2](BF4) (8 and 9) synthesized, as well as deprotonated and dearomatized in similar fashion. Reactivity studies revealed that the parent dicarbonyl complexes require more forceful conditions for H2 activation, compared with the monocarbonyl complexes. The ligand backbone was not found to participate in H2 activation and H2 ? hydride transfer to an organic substrate was not observed in either case. Density functional theory calculations revealed that the higher reactivity of the monocarbonyl complex in H2 splitting could be attributed to its higher affinity for H2. This behavior is attributed to two key points related to the requisite dI(Fe) ? sigma*(H2) back-bonding interaction in a conventional M-H2 Kubas interaction: (i) generally, the weaker pidonor capacity of the dicarbonyls, and (ii) specifically, the detrimental effect of a strongly piacidic CO ligand (versus weakly piacidic MeCN ligand) trans to the H2 activation site. The higher reactivity of the monocarbonyl complex is also evidenced by the catalytic transfer hydrogenation by monocarbonyl 8, whereas dicarbonyl 1 was ineffective. Overall, the results suggest that Nature uses the dicarbonyl motif in [Fe]-hydrogenase to diminish the interaction between the Fe center and dihydrogen, thereby preventing premature H2 activation prior to substrate (H4MPT+) binding and any resulting nonspecific hydride transfer reactivity.

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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 series of new C2-symmetric chiral aza crown ether macrocycles 1-4 have been synthesized from (S)-3-aryloxy-1,2-propanediol and (S)-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These new macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K up to 176.93 M-1 and DeltaG up to 12.81 kJ mol-1) by 1H NMR titration. These macrocyclic host exhibited enantioselective bonding toward the d-enantiomer of phenylalanine methyl ester hydrochloride with KD/KL up to 6.87 in CDCl3 with 0.25% CD3OD.

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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