Tag: M.W:600-700

Prein, Michael; Padwa, Albert published an article about the compound: Dirhodium(II) tetrakis(caprolactam)( cas:138984-26-6,SMILESS:C12=O[Rh+2]3(O=C4[N-]5CCCCC4)([N-]6C(CCCCC6)=O7)[N-](CCCCC8)C8=O[Rh+2]357[N-]1CCCCC2 ).Safety of Dirhodium(II) tetrakis(caprolactam). Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:138984-26-6) through the article.

The product distribution obtained from the Rh(II)-catalyzed decomposition of α-diazoimide MeO2CCH2NAcCOC(:N2)CO2Me can be selectively controlled by the proper choice of catalyst. While perfluorinated ligands favor isomuenchnone formation, products derived from six-membered ring cyclization are preferred using Rh2(OAc)4. The effect can be modulated by the addition Sc(OTf)3 as a Lewis acid.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Synthetic Route of C24H40N4O4Rh2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Dirhodium-catalyzed phenol and aniline oxidations with T-HYDRO. Substrate scope and mechanism of oxidation. Author is Ratnikov, Maxim O.; Farkas, Linda E.; McLaughlin, Emily C.; Chiou, Grace; Choi, Hojae; El-Khalafy, Sahar H.; Doyle, Michael P..

Dirhodium caprolactamate, Rh2(cap)4, is a very efficient catalyst for the generation of the tert-butylperoxy radical from tert-Bu hydroperoxide, and the tert-butylperoxy radical is a highly effective oxidant for phenols and anilines. These reactions are performed with 70% aqueous tert-Bu hydroperoxide using dirhodium caprolactamate in amounts ≥0.01 mol % to oxidize para-substituted phenols to 4-(tert-butyldioxy)cyclohexadienones. Although these transformations have normally been performed in halocarbon solvents, there is a significant rate enhancement when Rh2(cap)4-catalyzed phenol oxidations are performed in toluene or chlorobenzene. Electron-rich and electron-poor phenolic substrates undergo selective oxidation in good to excellent yields, but steric influences from bulky para substituents force oxidation onto the ortho position resulting in ortho-quinones. Comparative results with RuCl2(PPh3)3 and CuI are provided, and mechanistic comparisons are made between these catalysts that are based on diastereoselectivity (reactions with estrone), regioselectivity (reactions with p-tert-butylphenol), and chemoselectivity in the formation of 4-(tert-butyldioxy)cyclohexadienones. The data obtained are consistent with hydrogen atom abstraction by the tert-butylperoxy radical followed by radical combination between the phenoxy radical and the tert-butylperoxy radical. Under similar reaction conditions, para-substituted anilines are oxidized to nitroarenes in good yield, presumably through the corresponding nitrosoarene, and primary amines are oxidized to carbonyl compounds by TBHP in the presence of catalytic amounts of Rh2(cap)4.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Cumyl: A better N-protecting group of α-diazo acetamides for intramolecular C-H insertion reaction and its application in the synthesis of pregabalin and 3-benzyloxy pyrrolidine.Safety of Dirhodium(II) tetrakis(caprolactam).

Via intramol. C-H insertion of N-cumyl α-diazo acetamides, γ-lactams were efficiently synthesized with excellent regioselectivity. A concise route for the preparation of pregabalin (79% overall yield) and 3-benzyloxy pyrrolidine (21% overall yield) were reported.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Formula: C24H40N4O4Rh2. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Mild Dirhodium(II)-Catalyzed Chemo- and Regioselective Azidation of Arenes.

A mild chemo- and regioselective aromatic azidation reaction catalyzed by a dirhodium(II) catalyst with Zhdankin’s reagent as the azide source is described. A variety of functional groups were well tolerated under the reaction conditions. Mechanistic studies suggested that the Rh2(II,II)-bound azide intermediate, rather than the free azide radical, is the key active species in the reaction.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Stereoselective Intramolecular 1,3 C-H Insertion in Rh(II) Carbene Reactions, the main research direction is cyclopropane polysubstituted spirocyclic stereoselective preparation; diazo ketone ester tosyl preparation stereoselective intramol insertion rhodium.HPLC of Formula: 138984-26-6.

1,3 C-H insertion has been found to be a predominant reaction pathway in the Rh(II)-mediated cyclization of β-tosyl α-diazo carbonyl compounds I [R1 = Me, Et, n-Pr, R2 = H, R3 = Me, EtO, Ph; R1R2 = (CH2)4, (CH2)5, R3 = EtO; Ts = 4-MeC6H4SO2], which gave polysubstituted and spirocyclic cyclopropanes II stereoselectively.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Application of 138984-26-6. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Competitive Hydrogen Atom Transfer to Oxyl- and Peroxyl Radicals in the Cu-Catalyzed Oxidative Coupling of N-Aryl Tetrahydroisoquinolines Using tert-Butyl Hydroperoxide. Author is Boess, Esther; Wolf, Larry M.; Malakar, Santanu; Salamone, Michela; Bietti, Massimo; Thiel, Walter; Klussmann, Martin.

The question of whether hydrogen atom transfer (HAT) or electron transfer (ET) is the key step in the activation of N-aryl tetrahydroisoquinolines in oxidative coupling reactions using CuBr as catalyst and tert-Bu hydroperoxide (tBuOOH) has been investigated. Strong indications for a HAT mechanism were derived by using different para-substituted N-aryl tetrahydroisoquinolines, showing that electronic effects play a minor role in the reaction. Hammett plots of the Cu-catalyzed reaction, a direct time-resolved kinetic study with in situ generated cumyloxyl radicals, as well as d. functional calculations gave essentially the same results. We conclude from these results and from kinetic isotope effect experiments that HAT is mostly mediated by tert-butoxyl radicals and only to a lesser extent by tert-butylperoxyl radicals, in contrast to common assumptions. However, reaction conditions affect the competition between these two pathways, which can significantly change the magnitude of kinetic isotope effects.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Synthetic Route of C24H40N4O4Rh2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Intramolecular C-H insertion using NHC-di-rhodium(II) complexes: the influence of axial coordination. Author is Gomes, Luis F. R.; Trindade, Alexandre F.; Candeias, Nuno R.; Gois, Pedro M. P.; Afonso, Carlos A. M..

In this work we show that the intramol. C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes can be highly influenced by the axial ligand on the di-rhodium(II) complex. Axially monocoordinated NHC-Rh2(OAc)4 complexes have a distinct reactivity from the parent Rh2(OAc)4 complex affording the cyclization products in different rates and selectivities. Surprisingly, a new reaction mode emerged when using these complexes which led to a decarbonylation pathway.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Chiral Catalyst Controlled Diastereoselection and Regioselection in Intramolecular Carbon-Hydrogen Insertion Reactions of Diazoacetates》. Authors are Doyle, Michael P.; Kalinin, Alexey V.; Ene, Doina G..The article about the compound:Dirhodium(II) tetrakis(caprolactam)cas:138984-26-6,SMILESS:C12=O[Rh+2]3(O=C4[N-]5CCCCC4)([N-]6C(CCCCC6)=O7)[N-](CCCCC8)C8=O[Rh+2]357[N-]1CCCCC2).Synthetic Route of C24H40N4O4Rh2. Through the article, more information about this compound (cas:138984-26-6) is conveyed.

Individual enantiomers of substituted cyclohexyl diazoacetates or 2-octyl diazoacetates matched with a configurationally suitable chiral dirhodium(II) carboxamidate catalyst provide an effective methodol. for the synthesis of lactones with exceptional diastereo- and regiocontrol. Enantiomerically pure (1S,2R)-cis-2-methylcyclohexyl diazoacetate forms the all-cis-(1R,5R,9R)-9-methyl-2-oxabicyclo[4.3.0]nonan-3-one with complete diastereocontrol in reactions catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenylpropanoyl)-2-oxoimidazolidine-4(R)-carboxylate], Rh2(4(S)-MPPIM)4, but the configurational mismatch results in a mixture of products. The same diazoacetate produces (1S,5R)-5-methyl-2-oxabicyclo[4.3.0]nonan-3-one with virtually complete selectivity by catalysis with dirhodium(II) tetrakis[methyl 2-oxopyrrolidine-5(S)-carboxylate], Rh2(5(S)-MEPY)4. Similarly high stereo- and regiocontrol is also achieved with enantiomerically pure trans-2-methylcyclohexyl diazoacetates. Product control from insertion reactions of d- or l-menthyl diazoacetate and (+)-neomenthyl diazoacetate from the configurational match with dirhodium(II) catalyst results in the formation of one C-H insertion product in high yield. The exceedingly high product diastereoselection observed in these reactions is consistent with virtually exclusive insertion into equatorial C-H bonds. The catalyst-dependent selective formation of a cis-disubstituted γ-butyrolactone or a β-lactone from 2-octyl diazoacetate has been achieved. Control of product diastereoselectivity and regioselectivity in C-H insertion reactions is explained by conformational suitability in configurational match/mismatch of catalyst and carbene.

As far as I know, this compound(138984-26-6)Synthetic Route of C24H40N4O4Rh2 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Application of 138984-26-6. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Competitive Hydrogen Atom Transfer to Oxyl- and Peroxyl Radicals in the Cu-Catalyzed Oxidative Coupling of N-Aryl Tetrahydroisoquinolines Using tert-Butyl Hydroperoxide. Author is Boess, Esther; Wolf, Larry M.; Malakar, Santanu; Salamone, Michela; Bietti, Massimo; Thiel, Walter; Klussmann, Martin.

The question of whether hydrogen atom transfer (HAT) or electron transfer (ET) is the key step in the activation of N-aryl tetrahydroisoquinolines in oxidative coupling reactions using CuBr as catalyst and tert-Bu hydroperoxide (tBuOOH) has been investigated. Strong indications for a HAT mechanism were derived by using different para-substituted N-aryl tetrahydroisoquinolines, showing that electronic effects play a minor role in the reaction. Hammett plots of the Cu-catalyzed reaction, a direct time-resolved kinetic study with in situ generated cumyloxyl radicals, as well as d. functional calculations gave essentially the same results. We conclude from these results and from kinetic isotope effect experiments that HAT is mostly mediated by tert-butoxyl radicals and only to a lesser extent by tert-butylperoxyl radicals, in contrast to common assumptions. However, reaction conditions affect the competition between these two pathways, which can significantly change the magnitude of kinetic isotope effects.

This literature about this compound(138984-26-6)Application of 138984-26-6has given us a lot of inspiration, and I hope that the research on this compound(Dirhodium(II) tetrakis(caprolactam)) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Synthetic Route of C24H40N4O4Rh2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Dirhodium(II) tetrakis(caprolactam), is researched, Molecular C24H40N4O4Rh2, CAS is 138984-26-6, about Intramolecular C-H insertion using NHC-di-rhodium(II) complexes: the influence of axial coordination. Author is Gomes, Luis F. R.; Trindade, Alexandre F.; Candeias, Nuno R.; Gois, Pedro M. P.; Afonso, Carlos A. M..

In this work we show that the intramol. C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes can be highly influenced by the axial ligand on the di-rhodium(II) complex. Axially monocoordinated NHC-Rh2(OAc)4 complexes have a distinct reactivity from the parent Rh2(OAc)4 complex affording the cyclization products in different rates and selectivities. Surprisingly, a new reaction mode emerged when using these complexes which led to a decarbonylation pathway.

This literature about this compound(138984-26-6)Synthetic Route of C24H40N4O4Rh2has given us a lot of inspiration, and I hope that the research on this compound(Dirhodium(II) tetrakis(caprolactam)) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI