Month: April 2022

Synthetic Route of C14H8BF4Rh. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Rh(I)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates. Author is Bao, Robert Li-Yuan; Yin, Junjie; Shi, Lei; Zheng, Limin.

An asym. intermol. [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(I)-chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee [e.g., di-Me acetylenedicarboxylate + (E)-1,3-nonadiene → I (96%, 99% ee)]. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

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Quinuclidine – Wikipedia,
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Recommanded Product: 36620-11-8. 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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds.

A highly enantioselective hydrogenation of exocyclic α,β-unsaturated carbonyl compounds I (X = O, CH2, N-Boc; L = bond, CH2; R = Ph, 4-MeOC6H4, 2-naphthyl, etc.) catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) has been developed, giving the corresponding α-chiral cyclic lactones, lactams and ketones II with high yields and excellent enantioselectivities (up to 99% yield and 99% ee). Remarkably, the hydrogen bond between the substrate and the catalyst plays a critical role in this transformation. The synthetic utility of this protocol has been demonstrated by efficient synthesis of chiral 3-(4-fluorobenzyl)piperidine, a key chiral fragment of bioactive mols.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Category: quinuclidine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters. Author is Salnikov, Oleg G.; Chukanov, Nikita V.; Shchepin, Roman V.; Manzanera Esteve, Isaac V.; Kovtunov, Kirill V.; Koptyug, Igor V.; Chekmenev, Eduard Y..

13C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging mol. contrast agents for magnetic resonance imaging (MRI) visualization of various diseases, including cancer. Here, we present a systematic study of 1H and 13C parahydrogen-induced polarization of acetate and pyruvate esters with Et, Pr, and allyl alc. moieties. It was found that allyl pyruvate is the most efficiently hyperpolarized compound from those under study, yielding 21 and 5.4% polarization of 1H and 13C nuclei, resp., in CD3OD solutions Allyl pyruvate and Et acetate were also hyperpolarized in the aqueous phase using homogeneous hydrogenation with parahydrogen over a water-soluble rhodium catalyst. 13C polarization values of 0.82 and 2.1% were obtained for allyl pyruvate and Et acetate, resp. 13C-hyperpolarized methanolic and aqueous solutions of allyl pyruvate and Et acetate were employed for in vitro MRI visualization, demonstrating the prospects for translation of the presented approach to biomedical in vivo studies.

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Quinuclidine – Wikipedia,
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Itoda, Marino; Naganawa, Yuki; Ito, Makoto; Nonaka, Hiroshi; Sando, Shinsuke published the article 《Structural exploration of rhodium catalysts and their kinetic studies for efficient parahydrogen-induced polarization by side arm hydrogenation》. Keywords: rhodium catalyst PHIP efficiency side arm hydrogenation kinetics.They researched the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ).COA of Formula: C14H8BF4Rh. 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:36620-11-8) here.

Parahydrogen-induced polarization (PHIP) is a rapid and cost-effective hyperpolarization technique using transition metal-catalyzed hydrogenation with parahydrogen. We examined rhodium catalysts and their kinetic studies, rarely considered in the research of current PHIP. It emerged that rhodium complexes with electron-donating bisphosphine ligands, with a dicyclohexylphosphino group, appear to be more effective than conventional rhodium catalysts.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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: 36620-11-8, is researched, Molecular C14H8BF4Rh, about A Gallium-based Chiral Solvating Agent Enables the Use of 1H NMR Spectroscopy to Differentiate Chiral Alcohols, the main research direction is gallium differentiate alc NMR spectroscopy; Analytical Chemistry; Chemistry; Chirality in Analytical Chemistry; Stereochemistry.Electric Literature of C14H8BF4Rh.

In situ, direct 1H NMR chiral anal. by using chiral solvating agents is a convenient and efficient anal. technique. Here we developed a Ga-based chiral anionic metal complex for 1H NMR chiral anal. of alcs. Utilizing the optimal pKa value, the Ga complex was able to differentiate 1H NMR signals of each (R)- and (S)-enantiomer of alcs., measured at room temperature This direct 1H NMR chiral anal. of alcs. was used to rapidly determine enantiomeric excess and conversion in a kinetic resolution and an asym. synthesis.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation, the main research direction is chiral beta borylated carboxylic ester preparation rhodium catalyzed hydrogenation; ZhaoPhos rhodium bisphosphine thiourea catalyzed asym hydrogenation boryl ester; beta substituted boryl unsaturated ester rhodium bisphosphine thiourea hydrogenation; borylated carboxylic ester beta chiral preparation.COA of Formula: C14H8BF4Rh.

Rh/bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asym. hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asym. hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C = 2000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as Me (S)-3-hydroxy-3-phenylpropanoate and Me (S)-3-(furan-2-yl)-3-phenylpropanoate.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate(SMILESS: ClC1=C(N2N=C3[N+]([C@@]4([H])[C@@](CC5=C4C=CC=C5)([H])OC3)=C2)C(Cl)=CC(Cl)=C1.F[B-](F)(F)F,cas:1214711-48-4) is researched.Recommanded Product: 707-61-9. The article 《Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis》 in relation to this compound, is published in Angewandte Chemie, International Edition. Let’s take a look at the latest research on this compound (cas:1214711-48-4).

In the presence of the indenooxazinotriazolium carbene precursor I•BF4-, aliphatic aldehydes such as hydrocinnamaldehydes 4-RC6H4CH2CH2CHO (R = H, Br) underwent chemo- and enantioselective oxidative fluorination with N-fluorobenzenesulfonimide (NFSI) with alcs. such as cyclohexanol to give nonracemic α-fluoroesters such as II in 71-89% yields and in 73-98% ee. II (R = H) was hydrolyzed to its parent acid, converted to an N-benzyl-β-fluoroamine, and reduced to a β-fluoro alc.; II (R = Br) underwent Suzuki coupling to give II (R = Ph).

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 36620-11-8, is researched, SMILESS is [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10, Molecular C14H8BF4RhJournal, Article, Dalton Transactions called Investigation of the rhodium-catalyzed hydroboration of NHC-boranes: the role of alkene coordination and the origin of enantioselectivity, Author is Nava, Paola; Toure, Momar; Abdou Mohamed, Amel; Parrain, Jean-Luc; Chuzel, Olivier, the main research direction is mechanism potential energy surface calculation hydroboration allylimidazolylidene NHC borane; rhodium catalyst intramol enantioselective hydroboration allylimidazolylidene borane.Reference of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

The mechanism of the intramol. enantioselective rhodium(I)-catalyzed hydroboration of NHC-boranes is investigated by exptl. reactivity measurements and mol. electronic structure calculations, within the framework of the D. Functional Theory and the RPA methods. The crucial role of alkene coordination and the origin of enantioselectivity are discussed. Two possible mechanisms are considered, via either prior hydride migratory insertion or boron migratory insertion. The min. energy computed pathway leads to the enantiomer exptl. observed, therefore supporting the hydride migratory insertion mechanism. Calculations of the final steps of the catalytic cycle, i.e. regeneration of the catalyst and release of the product, give us further insights into the mechanism and rationalize the exptl. results.

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Quinuclidine – Wikipedia,
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Name: Bis(norbornadiene)rhodium (I) tetrafluoroborate. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration. Author is Chakrabarty, Suman; Palencia, Hector; Morton, Martha D.; Carr, Ryan O.; Takacs, James M..

Allylic and homoallylic phosphonates bearing an aryl or heteroaryl substituent at the γ- or δ-position undergo rhodium-catalyzed asym. hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99 : 1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asym. hydroboration (CAHB) of more highly functionalized internal alkenes. Phosphonate substrates bearing a variety of common heterocyclic ring systems, including furan, indole, pyrrole and thiophene derivatives, as well as those bearing basic nitrogen substituents (e.g., morpholine and pyrazine) are tolerated, although donor substituents positioned in close proximity of the alkene can influence the course of the reaction. Stereoisomeric (E)- and (Z)-substrates afford the same major enantiomer of the borated product. Deuterium-labeling studies reveal that rapid (Z)- to (E)-alkene isomerization accounts for the observed (E/Z)-stereoconvergence during CAHB. The synthetic utility of the chiral boronic ester products is illustrated by stereospecific C-B bond transformations including stereoretentive electrophile promoted 1,2-B-to-C migrations, stereoinvertive SE2 reactions of boron-ate complexes with electrophiles, and stereoretentive palladium- and rhodium-catalyzed cross-coupling protocols.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate( cas:1214711-48-4 ) is researched.Application In Synthesis of (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate.Lin, Qiqiao; Li, Yuanzhen; Das, Deb Kumar; Zhang, Guoxiang; Zhao, Zhifei; Yang, Shuang; Fang, Xinqiang published the article 《N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter Reaction》 about this compound( cas:1214711-48-4 ) in Chemical Communications (Cambridge, United Kingdom). Keywords: desymmetrization diene Stetter reaction heterocyclic carbene catalyst; asym desymmetrization diene heterocyclic carbene catalyst; ketone cyclic enantioselective synthesis; Stetter umpolung reaction asym desymmetrization diene. Let’s learn more about this compound (cas:1214711-48-4).

The asym. desymmetrization of 1,4-dienes via chiral N-heterocyclic carbene catalyzed Stetter-type umpolung reaction was demonstrated. A variety of differently substituted dienes were tolerated very well, affording cyclic ketones with two consecutive stereogenic centers (including one quaternary carbon) in moderate to high yields and with high to excellent enantioselectivities. This work expanded both reaction types of catalytic diene desymmetrizations and substrate diversity in NHC catalyzed desym. transformations.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider