16574-36-0Relevant academic research and scientific papers
CO2-Controlled Reductive Amination Reactions with NaBH4
Petersen, Allan R.,Lauridsen, Jerik Mathew Valera,Lee, Ji-Woong
, p. 7368 - 7372 (2020)
We report the use of CO2 to curb the reactivity of NaBH4 enabling its use in reductive amination reactions. CO2 readily reacts with NaBH4 to decrease its capacity to reduce aldehydes to alcohols while remaining able to reduce imines and iminium ions for desired alkylation reactions. The formation of NaBH(OCHO)3 as a reducing reagent was critical to achieve the desired selectivity. A general protocol was established for C–N bond formation reactions and replacing NaBH4 with NaBD4 allowed for reductive amination with concomitant deuteration to be carried out.
Consecutive β,β′-Selective C(sp3)?H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6F5)3
Fang, Huaquan,Xie, Kaixue,Kemper, Sebastian,Oestreich, Martin
supporting information, p. 8542 - 8546 (2021/03/08)
Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp3)?H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4-silapiperidines in decent yields. The multi-step reaction cascade involves amine-to-enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter- and one intramolecular.
METHOD OF INHIBITING APOLIPOPROTEIN-E EXPRESSION WHILE INCREASING EXPRESSION OF AT LEAST ONE OF LDL-RECEPTOR PROTEIN OR ABCA1 PROTEIN COMPRISING ADMINISTERING A SMALL COMPOUND
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Paragraph 0059; 0060, (2018/04/19)
This invention offers an effective method of decreasing expression of apolipoprotein E and increasing expression of at least one of either LDL-receptor protein or AbcA1 protein including selecting mammalian cells expressing apoE and at least one of either LDL-receptor protein or AbcA1 protein, contacting the mammalian cell with an effective amount of a compound having general formula (I) or general formula (II) in an amount sufficient to decrease expression of the apoE and increase expression of at least one of the LDL-receptor protein or the AbcA1 protein in the mammalian cell.
Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N,N-Dimethylformamide as Dimethylamino Source, Reductant and Solvent
Yang, Luo,Lin, Jie,Kang, Lei,Zhou, Wang,Ma, Da-You
supporting information, p. 485 - 490 (2018/01/15)
A practical zinc acetate dihydrate-catalyzed reductive amination of various carbonyl compounds with N,N-dimethylformamide (DMF) as dimethylamino (Me2N) source, reductant and solvent has been developed. This reaction shows broad substrate scope,
C-N Coupling of nitrogen nucleophiles with aryl and heteroaryl bromides using aminoarenethiolato-copper(I) (pre-)catalyst
Sperotto, Elena,van Klink, Gerard P.M.,de Vries, Johannes G.,van Koten, Gerard
experimental part, p. 3478 - 3484 (2010/07/02)
The activity of a library of 2-aminoarenethiolato-copper(I) (CuSAr) (pre-)catalyst was explored in the arylation reaction of amines and N-containing heterocycles with aryl and heteroaryl bromides, respectively. These CuSAr pre-catalysts are thermally stable, are soluble in common organic solvents and show good catalytic activities in these N-arylation reactions with catalyst loadings amounting to 2.5 mol %. The targeted C-N coupling products were obtained in moderate to good yields (40-97%) for a variety of substrates.
Reductive amination of aldehydes using aminoboranes as iminium ion generators
Suginome, Michinori,Tanaka, Yusuke,Hasui, Tomoaki
, p. 1047 - 1050 (2007/10/03)
2-Dialkylamino-4H-1,3,2-benzodioxaborins, salicyl alcohol derived aminoboranes, serve as efficient and mild iminium ion generators in the reductive animation of aldehydes with NaBH4. Using a diisopropylamino derivative, a variety of amines including secondary and primary amines, and ammonia can participate to the reductive amination in aprotic organic solvents without the use of acidic promoters. Georg Thieme Verlag Stuttgart.
Titanocene-catalyzed coupling of aromatic amides in the presence of organosilanes: A novel route to vicinal diamines and a new class of amine-substituted oligomers
Rangareddy, Kesamreddy,Selvakumar, Kumaravel,Harrod, John F.
, p. 6843 - 6850 (2007/10/03)
The title reaction has been surveyed for a number of substrates with differing substitution patterns. With a few exceptions, the methodology provides a one-pot synthesis of the 1,2-diamines from widely available and inexpensive starting materials, and in high yields. In addition, the coupling of 1,4-and 1,3-bis-(N,N,N′,N′-tetraalkyl)arylenediamides is shown, under the same experimental conditions, to yield oligomers: R2NC(O)C 6H4CH(NR2)-[CH(NR2)C 6H4CH(NR2)]n-CH(NR 2)C6H4C(O)-NR2 (R = methyl and ethyl; n = 0 to ca. 5). The chemical structures of these unprecedented oligomers are determined by comparison of NMR and MS spectra to those of vicinal diamines, prepared from the analogous N,N-dialkylbenzamides. The origin of the limitation of oligomer chain length is probably due to a specific effect of the internal benzylic amine group, since the substrate 4-Me2NCH 2C6H4C(O)NMe2 was found to be uniquely unreactive compared to the other 4-substituted N,N-dialkylbenzamides investigated. N-Methylphthalimide was briefly studied as a monomer and analysis by MS showed that oligomers are formed. Attempts to fully characterize these polymers were unsuccessful.
