Tag: M.W:400-500

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide( cas:313342-24-4 ) is researched.Recommanded Product: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide.Dub, Pavel A.; Wang, Hui; Matsunami, Asuka; Gridnev, Ilya D.; Kuwata, Shigeki; Ikariya, Takao published the article 《C-F bond breaking through aromatic nucleophilic substitution with a hydroxo ligand mediated via water bifunctional activation》 about this compound( cas:313342-24-4 ) in Bulletin of the Chemical Society of Japan. Keywords: cyclometalated oxobenzenesulfonyldiamido ruthenium complex preparation crystal structure DFT; crystal structure cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex; mol structure cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex; hydration reaction benzenesulfonyldiamido ruthenium iridium complex DFT; optimized geometry cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex DFT. Let’s learn more about this compound (cas:313342-24-4).

Transformation of C-F to C-O bond mediated by bifunctional Ru and Ir complexes is described. This reaction proceeds through water O-H bond cleavage via metal-ligand cooperation in the newly developed 16e bifunctional Ru and Ir complexes bearing chiral (S,S)-C6F5SO2-dpen ligand. The 16e Ru amido complex, [Ru{(S,S)-Pfbsdpen}(η6-hmb)] (1a), readily reacted with H2O at room temperature producing oxometallacyclic compound, (R)-[Ru{κ3(N,N’,O)-(S,S)-OC6F4SO2dpen}(η6-hmb)] (3aR), as a result of bifunctional H2O activation followed by ortho-oxometalation via SNAr. Complex 3aR can be prepared either from 1a or, more conveniently from its 18e chlorido precursor, complex (R)-[RuCl{(S,S)-Pfbsdpen}(η6-hmb)]. On the contrary, the 16e Ir amido complex, [Cp*Ir{(S,S)-Pfbsdpen}] (2), is kinetically stable toward H2O at room temperature Oxometallacyclic compound (R)-[Cp*Ir{κ3(N,N’,O)-(S,S)-OC6F4SO2dpen}] (4R) was prepared in high yield by the reaction of [Cp*IrCl2]2 with 2 equiv of (S,S)-Pfbsdpen in the presence of KOH under reflux in THF. In either case 3R or 4R was obtained as a single diastereomer, the structure of which was determined by single-crystal x-ray diffraction studies in solid state and NMR-anal. in solution Reaction mechanism was studied by NMR spectroscopy combined with continuum solvent reaction-field d. functional theory (DFT) anal. Exptl. studies showed that diastereoselective oxocyclometalation 1a → 3aR proceeds at temperatures >0° in a stepwise manner through the detectable intermediate, hydroxo complex (R)-[Ru(OH){(S,S)-Pfbsdpen}(η6-hmb)] (6aR), which exists in equilibrium with less-populated diastereomer (S)-[Ru(OH){(S,S)-Pfbsdpen}(η6-hmb)] (6aS) in 10:1 ratio at -80° in CD2Cl2. Computational anal. essentially explains the diastereoselectivity in this reaction via a significant difference in the stabilities of the corresponding transition states: although diastereomers 6aR and 6aS are in equilibrium via complex 1a, only 6aR is transformed into 3aR via rate-determining Meisenheimer-type transition state.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 313342-24-4, is researched, Molecular C20H15F5N2O2S, about Enantioselective reduction of α-cyano and α-nitro substituted acetophenones promoted by a bifunctional mesoporous silica, the main research direction is cyanoacetophenone nitroacetophenone reduction silica supported iridium; benzylic alc asym preparation; silica supported iridium enantioselective reduction catalyst.Product Details of 313342-24-4.

Disclosed is a method for enantioselective reduction of α-cyano- and α-nitroacetophenones using a bifunctional mesoporous silica supported iridium catalyst. For example, α-cyanoacetophenone underwent iridium-catalyzed enantioselective reduction to give (S)-2-cyano-1-phenylethanol.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide(SMILESS: O=S(C1=C(F)C(F)=C(F)C(F)=C1F)(N[C@@H](C2=CC=CC=C2)[C@@H](N)C3=CC=CC=C3)=O,cas:313342-24-4) is researched.Name: (S)-Butan-2-ol. The article 《Accessible Bifunctional Oxy-Tethered Ruthenium(II) Catalysts for Asymmetric Transfer Hydrogenation》 in relation to this compound, is published in Organic Letters. Let’s take a look at the latest research on this compound (cas:313342-24-4).

A concise synthesis of new oxy-tethered ruthenium complexes effective for the asym. transfer hydrogenation of aromatic ketones is described. The oxy-tether was constructed via a defluorinative etherification arising from an intramol. nucleophilic substitution of a perfluorinated phenylsulfonyl substituent. The obtained tethered complexes exhibited desirable catalytic activity and selectivity, especially in the asym. transfer hydrogenation of functionalized aromatic ketones. The robustness and rigidity of the tether contribute to their superior catalytic performance relative to the nontethered prototype complex.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

HPLC of Formula: 313342-24-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, is researched, Molecular C20H15F5N2O2S, CAS is 313342-24-4, about Reaction Development and Mechanistic Study of a Ruthenium Catalyzed Intramolecular Asymmetric Reductive Amination en Route to the Dual Orexin Inhibitor Suvorexant (MK-4305). Author is Strotman, Neil A.; Baxter, Carl A.; Brands, Karel M. J.; Cleator, Ed; Krska, Shane W.; Reamer, Robert A.; Wallace, Debra J.; Wright, Timothy J..

The 1st example of an intramol. asym. reductive amination of a dialkyl ketone with an aliphatic amine was developed for the synthesis of Suvorexant (MK-4305), a potent dual Orexin antagonist under development for the treatment of sleep disorders. This challenging transformation is mediated by a novel Ru-based transfer hydrogenation catalyst that provides the desired diazepane ring in 97% yield and 94.5% ee. Mechanistic studies revealed that CO2, produced as a necessary byproduct of this transfer hydrogenation reaction, has pronounced effects on the efficiency of the Ru catalyst, the form of the amine product, and the kinetics of the transformation. A simple kinetic model explains how product inhibition by CO2 leads to overall 1st-order kinetics, but yields an apparent zero-order dependence on initial substrate concentration The deleterious effects of CO2 on reaction rates and product isolation can be overcome by purging CO2 from the system. The transfer hydrogenation of acetophenone with this same catalyst system was examined The rate of ketone hydrogenation was greatly accelerated by purging of CO2 or trapping with nucleophilic secondary amines.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Transfer hydrogenation in water: enantioselective, catalytic reduction of (E)-β,β-disubstituted nitroalkenes, published in 2009-09-17, which mentions a compound: 313342-24-4, Name is N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, Molecular C20H15F5N2O2S, Category: tetrahydrofurans.

A mild catalytic asym. transfer hydrogenation of β,β-disubstituted nitroalkenes is reported. Formic acid is used as a reductant in combination with an Ir catalyst. The reaction is conducted in water at low pH and open to air to give adducts in preparatively useful yield and selectivity.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, is researched, Molecular C20H15F5N2O2S, CAS is 313342-24-4, about Ir(III) complexes of diamine ligands for asymmetric ketone hydrogenation, the main research direction is arylalkanol asym preparation; arylketone asym hydrogenation iridium chiral diamine; chiral diaminepreparation iridium asym hydrogenation catalyst; diamine sulfonylation reductive amination.Quality Control of N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide.

The use of a combination of IrCl3 with a series of ligands derived from the C2-sym. diamine diphenylethanediamine (DPEN) forms a catalyst capable of the asym. hydrogenation of ketones in up to 85% ee.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Quality Control of N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, is researched, Molecular C20H15F5N2O2S, CAS is 313342-24-4, about Oxy-tethered Cp*Ir(III) complex as a competent catalyst for selective dehydrogenation from formic acid. Author is Nakamura, Hitomi; Yoshida, Minori; Matsunami, Asuka; Kuwata, Shigeki; Kayaki, Yoshihito.

A bifunctional tethered iridium catalyst containing a 1,2-diphenylethylenediamine framework was synthesized for the first time. The ethereal tether chain was easily constructed via the intramol. oxydefluorination of a perfluorophenylsulfonyl substituent by using a modified 1,2,3,4,5-pentamethylcyclopentadienyl ligand with a hydroxyalkyl chain. The conformationally constrained structure could hamper deactivation pathways in the catalytic hydrogen generation from formic acid, leading to advanced durability and complete conversion.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Matsunami, Asuka; Kayaki, Yoshihito; Kuwata, Shigeki; Ikariya, Takao published the article 《Nucleophilic Aromatic Substitution in Hydrodefluorination Exemplified by Hydridoiridium(III) Complexes with Fluorinated Phenylsulfonyl-1,2-diphenylethylenediamine Ligands》. Keywords: nucleophilic aromatic substitution hydrodefluorination hydridoiridium fluorinated phenylsulfonyldiphenylethylenediamine ligand; pentamethylcyclopentadienyliridium penfluorophenylsulfonyldiphenylethylenediamine hydride nucleophilic aromatic substitution; crystal mol structure pentamethylcyclopentadienyliridium penfluorophenylsulfonyldiphenylethylenediamine.They researched the compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide( cas:313342-24-4 ).Application In Synthesis of N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:313342-24-4) here.

In connection with the mechanism of the catalytic reduction of fluoroarenes, the intramol. defluorinative transformation of a family of iridium hydrides utilized as a hydrogen transfer catalyst is studied. Hydridoiridium(III) complexes bearing fluorinated phenylsulfonyl-1,2-diphenylethylenediamine ligands are spontaneously converted into iridacycles via selective C-F bond cleavage at the ortho position. NMR spectroscopic studies and synthesis of intermediate model compounds verify the stepwise pathway involving intramol. substitution of the ortho-fluorine atom by the hydrido ligand, i.e., hydrodefluorination (HDF), and the following fluoride-assisted cyclometalation at the transiently formed C-H bond. A hydridoiridium complex with a 2,3,4,5,6-pentafluorophenylsulfonyl (Fs) substituent is more susceptible to HDF than its analog with a 2,3,4,5-tetrafluorophenylsulfonyl (FsH) group. The FsH-derivative clearly shows that C-F bond cleavage occurs in preference to C-H activation. These exptl. results firmly support the nucleophilic aromatic substitution (SNAr) mechanism in HDF by hydridoiridium species.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

HPLC of Formula: 313342-24-4. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, is researched, Molecular C20H15F5N2O2S, CAS is 313342-24-4, about Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis. Author is Miskov-Pajic, Vukoslava; Willig, Felix; Wanner, Daniel M.; Frey, Wolfgang; Peters, Rene.

Diels-Alder reactions have become established as one of the most effective ways to prepare stereochem. complex six-membered rings. Different catalysis concepts have been reported, including dienophile activation by Lewis acids or H-bond donors and diene activation by bases. Herein we report a new concept, in which an acidic prodiene is acidified by a Lewis acid to facilitate deprotonation by an imidazolium-aryloxide entity within a polyfunctional catalyst. A metal dienolate is thus formed, while an imidazolium-ArOH moiety probably forms hydrogen bonds with the dienophile. The catalyst type, readily prepared in few steps in high overall yield, was applied to 3-hydroxy-2-pyrone and 3-hydroxy-2-pyridone as well as cyclopentenone prodienes. Maleimide, maleic anhydride, and nitroolefin dienophiles were employed. Kinetic, spectroscopic, and control experiments support a cooperative mode of action. High enantioselectivity was observed even with unprecedented TONs of up to 3680.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Formula: C20H15F5N2O2S. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, is researched, Molecular C20H15F5N2O2S, CAS is 313342-24-4, about Cleavage of N-H Bond of Ammonia via Metal-Ligand Cooperation Enables Rational Design of a Conceptually New Noyori-Ikariya Catalyst. Author is Dub, Pavel A.; Matsunami, Asuka; Kuwata, Shigeki; Kayaki, Yoshihito.

The asym. transfer hydrogenation (ATH) of ketones/imines with Noyori-Ikariya catalyst represents an important reaction in both academia and fine chem. industry. The method allows for the preparation of chiral secondary alcs./amines with very good to excellent optical purities. Remarkably, the same chiral Noyori-Ikariya complex is also a precatalyst for a wide range of other chemo- and stereoselective reductive and oxidative transformations. Among them are enantioselective sulfonamidation of acrylates (intramol. aza-Michael reaction) and carboxylation of indoles with CO2. Development of these catalytic reactions has been inspired by the realized cleavage of the N-H bond of sulfonamides and indoles by the 16e- amido derivative of the 18e- precatalyst via metal-ligand cooperation (MLC). This paper summarizes our efforts to investigate N-H bond cleavage of gaseous ammonia in solution via MLC and reports the serendipitous discovery of a new class of chiral tridentate κ3[N,N’,N”] Ru and Ir metallacycles, derivatives of the famous M-FsDPEN catalysts (M = Ru, Ir). The protonation of these metallacycles by strong acids containing weakly coordinating (chiral) anions generates ionic complexes, which were identified as conceptually novel Noyori-Ikariya precatalysts. For example, the ATH of aromatic ketones with some of these complexes proceeds with up to 99% ee.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem