202199-03-9Relevant academic research and scientific papers
Synthesis and structures of copper(II) complexes containing N,N-bidentate N-substituted phenylethanamine derivatives as pre-catalysts for heterotactic-enriched polylactide
Cho, Juhyun,Chun, Min Kyung,Nayab, Saira,Jeong, Jong Hwa
, p. 54 - 62 (2019)
A series of Cu(II) complexes, [LnCuCl2]2 (Ln = (S)-N-((1H-pyrazol-1-yl)methyl)-1-phenylethanamine (L1), (S)-N-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-1-phenylethanamine (L2) and (S)-1-phenyl
Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray
Large, Benjamin,Meddeb, Maissa,Pucheta, José Enrique Herbert,Gaucher, Anne,Cordier, Marie,Gosmini, Corinne,Farjon, Jonathan,Auffrant, Audrey,Prim, Damien
supporting information, (2019/09/09)
The preparation of pyridylmethylamines (pma)-ZnBr2 and -CoBr2 complexes is described. Accurate structural informations in both solution and solid state have been obtained using an approach combining advanced NMR such as pure shift gr
Synthesis and characterization of aminopyridine iron(ii) chloride catalysts for isoprene polymerization: Sterically controlled monomer enchainment
Jing, Chuyang,Wang, Liang,Mahmood, Qaiser,Zhao, Mengmeng,Zhu, Guangqian,Zhang, Xianhui,Wang, Xiaowu,Wang, Qinggang
, p. 7862 - 7874 (2019/06/13)
In this study, a series of 2-R-6-(1-(alkylamino)methyl)pyridine-iron complexes [alkyl: (CPh3) Fe1H; (CHPh2) Fe2H; (CHPh2) Fe3Me; (CHMePh) Fe4H; (CH2Ph) Fe5H; (CHMe2) Fe6H; (C6H11) Fe7H; (CH2(4-OMe)Ph) Fe8H; (CH2(4-CF3)Ph) Fe9H; (CH2(2,4,6-Me3)Ph) Fe10H; (CH2Ph) Fe11Me] were synthesized and well characterized by ATR-IR spectroscopy, HRMS spectroscopy and elemental analysis. In addition, Fe3Me, Fe4H, Fe7H and Fe11Me were characterized by X-ray diffraction analysis: Fe3Me and Fe11Me adopted distorted tetrahedral geometries in the solid state while Fe4H and Fe7H were found in dimeric or polymeric forms respectively in which chlorides acted as bridging ligands. The catalytic capacities of these iron complexes were investigated for isoprene polymerization. Upon activation with a MAO cocatalyst, the catalytic activities of complexes varied as a function of the steric and electronic influences of substituents. In general, the catalysts bearing the least steric groups and electron-withdrawing groups exhibited relatively high activities. An outstanding activity of 190.6 × 104 g·mol-1·h-1 was obtained by Fe5H [CH2Ph]. Moreover, changes in the steric hindrance around the metal center showed a notable effect on the selectivity of monomer enchainment. In particular, most of the polymers obtained by these complexes bearing flexible frameworks were in favor of 3,4-enchainment.
Chiral Lithium Amido Zincates for Enantioselective 1,2-Additions: Auto-assembling Reagents Involving a Fully Recyclable Ligand
Rouen, Mathieu,Chaumont, Pauline,Barozzino-Consiglio, Gabriella,Maddaluno, Jacques,Harrison-Marchand, Anne
supporting information, p. 9238 - 9242 (2018/06/04)
A methodology consisting in carrying out enantioselective nucleophilic 1,2-additions (ee values up to 97 %) from cheap, easily accessible, and never described before, chiral lithium amido zincates is presented. These multicomponent reactants auto-assemble when mixing, in a 1:1 ratio, a homoleptic diorganozinc (R2Zn) with a chiral lithium amide (CLA). The latter, obtained after a single reductive amination, plays the role of the chiral inductor and is fully recoverable thanks to a simple acid–base wash, allowing being recycled and re-use without loss of stereochemical information.
New potentially dhelating chiral magnesium amide bases for use in enantioselective deprotonation reactions
Kerr, William J.,Middleditch, Michael,Watson, Allan J. B.
, p. 177 - 180 (2011/03/22)
A series of chiral secondary amines, incorporating a five- or six-membered heterocycle, were synthesised and used to prepare novel chiral magnesium bisamide reagents. These amide bases were subsequently applied within asymmetric deprotonation reactions to
Compositions for reductive aminations utilizing supported tricarboxyborohydride reagents and methods of using the same
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Page/Page column 11-14, (2011/08/06)
A modified solid-support for use as a supported reagent for use in reduction reactions, including reductive amination comprising a solid-support having an tetrasubstituted ammonium cation species ionically bonded to a borohydride anion species extending therefrom having the general formula: wherein P is a solid-support, S is a spacer group selected from the group consisting of alkylene, {including —(CH2)n—}, alkyleneoxy {including -0(CH2)n—}, alkylenethio {including —S(CH2)n—} and alkylenecarboxy, {including —O(O)C—(CH2)n—}, n=2-16. R1, R2, R3 and R are each independently selected from the group consisting of alkyl, cycloalkyl, haloalkyl and aryl. Y equals 1, 2 or 3. H is hydrogen or deuterium.
N-heterocyclic pyridylmethylamines: Synthesis, complexation, molecular structure, and application to asymmetric Suzuki-Miyaura and oxidative coupling reactions
Grach, Guillaume,Pieters, Gregory,Dinut, Aurelia,Terrasson, Vincent,Medimagh, Raouf,Bridoux, Alexandre,Razafimahaleo, Vanessa,Gaucher, Anne,Marque, Sylvain,Marrot, Jerome,Prim, Damien,Gil, Richard,Planas, Jose Giner,Vinas, Clara,Thomas, Isabelle,Roblin, Jean-Philippe,Troin, Yves
scheme or table, p. 4074 - 4086 (2011/10/03)
The synthesis of N,N-bidentate ligands based on a π-deficient N-heterocyclic pyridylmethylamine core is described. The preparation and characterization of the corresponding N,N-ligand-palladium complexes in solution and the solid state are illustrated. Pd complexes showed a good yield and moderate catalytic activity (up to 40% ee) in the asymmetric Suzuki-Miyaura coupling reaction, leading to methoxybinaphthyl derivatives. The combination of N,N-pyridylmethylamines with cuprous iodide revealed effective catalytic systems in oxidative naphthol derivative coupling reactions, affording the corresponding binaphthyls in high yields and with enantioselectivities of up to 61%.
Enantioselective Friedel-Crafts alkylation of indole derivatives catalyzed by new Yb(OTf)3-pyridylalkylamine complexes as chiral Lewis acids
Grach, Guillaume,Dinut, Aurelia,Marque, Sylvain,Marrot, Jerome,Gil, Richard,Prim, Damien
experimental part, p. 497 - 503 (2011/02/28)
New Yb(OTf)3-pyridylalkylamine complexes have been employed as chiral Lewis acids in the enantioselective Friedel-Crafts alkylation of indole derivatives with trifluoropyruvates. The influence of the substituents as well as the configuration of
Grignard allylic substitution catalyzed by imidazol-2-ylidene- and imidazol-4-ylidene-magnesium complexes
Okamoto, Sentaro,Ishikawa, Hiroyuki,Shibata, Yoshimi,Suhara, Yu-Ichiro
supporting information; experimental part, p. 5704 - 5707 (2010/11/16)
In the presence of a catalytic amount of 1,2-disubstituted or 1,2,3-trisubstituted imidazolium salts, γ-substituted allyl chlorides reacted with alkyl Grignard reagents to undergo substitution reactions in an SN2′-selective fashion, where the magnesium ate complexes [(N-heterocyclic carbene-MgR3)-(MgX)+] of imidazol-2-ylidenes or imidazol-4-ylidenes, generated in situ, were postulated as the active species. It was observed that the reactions with imidazol-4-ylidene catalysts were faster than those with imidazol-2-ylidenes. Enantioselective catalysis using a chiral imidazolium salt was preliminarily investigated.
Aminophosphinic acids in a pyridine series, Part 2: Synthesis of 2-, 3-, and 4-pyridyl derivatives of 1-(Benzylamino)-methyl-H-phosphinic Acids
Goldeman, Waldemar,Boduszek, Bogdan
experimental part, p. 1413 - 1425 (2010/03/24)
New 2-pyridyl, 3-pyridyl, and 4-pyridyl derivatives of 1-[N-(benzyl)amino]- methyl-H-phosphinic acid were prepared by the addition of bis(trimethylsilyl) phosphonite to the corresponding imines and subsequent methanolysis of the addition products. Treatment of the 2-pyridyl- and 1-(4-pyridyl)-1-(benzylamino) -methyl-H-phosphinic acids with aqueous mineral acids leads to cleavage and formation of the corresponding secondary amines and phosphorous acid (H3PO3).
