- Diazaphospholene Precatalysts for Imine and Conjugate Reductions
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The first examples of 1,3,2-diazaphospholene-catalyzed imine reduction and conjugate reduction reactions are reported. This approach employs readily synthesized alkoxydiazaphospholene precatalysts that can be handled in open air. Reduction of substrates containing Lewis basic functionality, isolated unsaturation, and protic functional groups was accomplished. The synthetic utility of this approach is demonstrated by the synthesis of the important antiparkinson medicine rasagiline and the natural product zingerone.
- Adams, Matt R.,Tien, Chieh-Hung,Huchenski, Blake S. N.,Ferguson, Michael J.,Speed, Alexander W. H.
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supporting information
p. 6268 - 6271
(2017/05/19)
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- Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
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The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.
- Muzalevskiy, Vasily M.,Ustynyuk, Yury A.,Gloriozov, Igor P.,Chertkov, Vyacheslav A.,Rulev, Alexander Yu.,Kondrashov, Evgeniy V.,Ushakov, Igor A.,Romanov, Alexey R.,Nenajdenko, Valentine G.
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p. 16982 - 16989
(2015/11/16)
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- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3
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A simple method for N-alkylation of 1, 2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/γ-Al2O 3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of 1, 2-diaminoethane with both primary and secondary alcohols. Mono-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols resulted in high yields; the yields of tetra-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols declined markedly with the increase of the molecular volume of alcohols.
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
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experimental part
p. 304 - 307
(2012/08/28)
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- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/?3-Al2O3
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A simple method for N-alkylation of 1,2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/?3-Al2O3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
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p. 304 - 307
(2015/03/03)
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- SATURATED N-HETEROCYCLIC CARBENE-LIGAND METAL COMPLEX DERIVATIVES, PREPARING METHOD THEREOF, AND PREPARING METHOD OF SILANE COMPOUND BY HYDROSILYLATION REACTION USING THE SAME AS CATALYST
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Provided are a saturated N-heterocyclic carbene-ligand metal complex derivative, a method for preparing the same, and a method for preparing a silane compound by hydrosilylation using the same as a catalyst. To describe in more detail, the metal complex derivative has a saturated N-heterocyclic carbene derivative and an olefin ligand at the same time. A silane compound is prepared by hydrosilylation in the presence of the metal complex derivative as a catalyst. The provided metal complex derivative of the present invention has superior stability during hydrosilylation reaction and is capable of effectively performing the hydrosilylation reaction at low temperature even with small quantity. Further, a product with superior regioselectivity may be obtained. In addition, after the hydrosilylation reaction is completed, the metal complex derivative may be recovered and recycled.
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Page/Page column 7; 8
(2011/07/08)
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- SATURATED N-HETEROCYCLIC CARBENE-LIGAND METAL COMPLEX DERIVATIVES, PREPARING METHOD THEREOF, AND PREPARING METHOD OF SILANE COMPOUND BY HYDROSILYLATION REACTION USING THE SAME AS CATALYST
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Provided are a saturated N-heterocyclic carbene-ligand metal complex derivative, a method for preparing the same, and a method for preparing a silane compound by hydrosilylation using the same as a catalyst. To describe in more detail, the metal complex derivative has a saturated N-heterocyclic carbene derivative and an olefin ligand at the same time. A silane compound is prepared by hydrosilylation in the presence of the metal complex derivative as a catalyst. The provided metal complex derivative of the present invention has superior stability during hydrosilylation reaction and is capable of effectively performing the hydrosilylation reaction at low temperature even with small quantity. Further, a product with superior regioselectivity may be obtained. In addition, after the hydrosilylation reaction is completed, the metal complex derivative may be recovered and recycled.
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Page/Page column 13
(2011/07/30)
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- Effect of ligand substituents in olefin polymerisation by half-sandwich titanium complexes containing monoanionic iminoimidazolidide ligands-MAO catalyst systems
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Various half-sandwich titanium complexes containing iminoimidazolidide ligands, CpTiCl2[1,3-R2(CH2N)2CN] (1a-d) [R = Ph (a), 2,6-Me2C6H3 (b), cyclohexyl (c), tBu (d)], have been employed as the catalyst precursors for ethylene polymerisation, syndiospecific styrene polymerisation, and copolymerisation of ethylene with 1-hexene in the presence of MAO cocatalyst; 1d showed the highest catalytic activity for ethylene polymerisation whereas 1b showed the highest activity for syndiospecific styrene polymerisation.
- Nomura, Kotohiro,Fukuda, Hiroya,Katao, Shohei,Fujiki, Michiya,Kim, Hyun Joon,Kim, Dong-Hyun,Zhang, Shu
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p. 7842 - 7849
(2011/09/20)
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- N,N′-dialkyl- and N-aIkyl-N-mesityl-substituted N-heterocyclic carbenes as ligands in Grubbs catalysts
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Various symmetrically and asymmetrically substituted N-heterocyclic carbene (NHC) ligands bearing aliphatic nitrogen-containing side groups have been synthesised. In our attempts to isolate the corresponding second-generation Grubbs catalysts, we were unsuccessful when using the symmetrical aliphatic NHC ligands. For the asymmetrical ligands bearing an aliphatic moiety on one side and an aromatic mesityl group on the other side, substitution of a phosphine ligand was achieved. The performance of a soformed series of Ru-based metathesis initiators has been evaluated for the ring-opening metathesis polymerisation (ROMP) of cycloocta-1,5-diene and the ring-dosing metathesis (RCM) of diethyl diallylmalonate.
- Ledoux, Nele,Allaert, Bart,Pattyn, Siegfried,Mierde, Hans Vander,Vercaemst, Carl,Verpoort, Francis
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p. 4654 - 4661
(2008/02/08)
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- METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE
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PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.
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Page/Page column 7; 8
(2010/02/11)
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- Preparation of chiral amine carbonyl chromium(0) complexes with [(norbornadiene)Cr(CO)4] as the complexation reagent
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A number of chiral amines were prepared and used as ligands in carbonylchromium(0) complexes. Included are monoamines chelating diamines and methionine methyl ester. For their complexation (norbornadiene)tetracarbonylchromium(0) was found to allow complex
- Strotmann, Markus,Butenschoen, Holger
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p. 2273 - 2284
(2007/10/03)
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- Zirconium borohydride - A versatile reducing agent for the reduction of electrophilic and nucleophilic substrates
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Zirconium borohydride, a potential reducing agent, reduces acids, esters, imines to the corresponding alcohols and secondary amines in good yield at room temperature within two hours. This facile reducing property was taken advantage off in the synthesis of pheromones and some novel chiral precursors for asymmetric synthesis.
- Narasimhan,Balakumar
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p. 4387 - 4395
(2007/10/03)
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- BORANE-TETRAHYDROFURAN AS A USEFUL REAGENT IN THE N-MONOALKYLATION OF AMINES AND AMINOALCOHOLS BY CARBONYL COMPOUNDS.
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A new procedure for the high-yield N-monoalkylation of primary aromatic and aliphatic amines is described.
- Morales, Hilda R.,Perez-Juarez, Martin,Cuellar, Laura,Mendoza, Lourdes,Fernandez, Hector,Contreras, Rosalinda
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p. 1213 - 1220
(2007/10/02)
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