Day: April 20, 2022

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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation.Quality Control of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

Rh-catalyzed asym. hydrogenation of prochiral substituted benzo[b]thiophene 1,1-dioxides was successfully developed, affording various chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides I (R = H, 6-MeO; R1 = C6H5, 4-MeOC6H4, 4-FC6H4, etc.; R2 = C6H5, 4-MeOC6H4, 3-H3CC6H4, etc.) with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). In particular, for challenging substrates, such as aryl substituted substrates with sterically hindered groups and alkyl substituted substrates, the reaction proceeded smoothly in catalytic system with excellent results. The gram-scale asym. hydrogenation proceeded well with 99% yield and 99% ee in the presence of 0.02 mol% (S/C = 5000) catalyst loading. The possible hydrogen-bonding interaction between the substrate and the ligand may play an important role in achieving high reactivity and excellent enantioselectivity.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Product Details of 36620-11-8. 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 HMF and furfural: Promising platform molecules in rhodium-catalyzed carbonylation reactions for the synthesis of furfuryl esters and tertiary amides. Author is Qi, Xinxin; Zhou, Rong; Ai, Han-Jun; Wu, Xiao-Feng.

A biomass involved rhodium-catalyzed carbonylative synthesis of furfuryl esters and tertiary amides has been developed. 5-Hydroxymethylfurfural (HMF) was used as both substrate and CO surrogate for the first time in a carbonylation reaction, and both alkyl and aryl iodides were tolerated well to afford the desired furfuryl esters in moderate to good yields. In addition, furfural was also utilized as a CO source for the synthesis of tertiary amides. A variety of tertiary amides were obtained in moderate to excellent yields with good functional groups compatibility. Notably, tertiary amines were used as the amine source through a C-N bond cleavage pathway in the absence of addnl. oxidant.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Category: quinuclidine. 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 Catalytic Asymmetric Hydrogenation of Tetrasubstituted Unsaturated Lactams: An Efficient Approach to Enantioenriched 3,4-Disubstituted Piperidines. Author is Yin, Congcong; Pan, Yingmin; Zhang, Xumu; Yin, Qin.

An unprecedented Rh-catalyzed enantioselective and diastereoselective hydrogenation of easily accessed α,β-disubstituted unsaturated lactams I (R = Ph, Me, cyclohexyl, thiophen-2-yl, etc.; R1 = Me, ethyl; X = 4-methoxyphenyl, benzyl, methyl) to afford synthetically valuable chiral lactams II with 1,2-consecutive stereocenters was reported. The reaction could be performed on gram scale and the products could be concisely transformed to enantiomerically pure trans-3,4-disubstitituted piperidines [such as (+)-femoxetin, (-)-paroxetine] which are prevalent structural units existed in medicinal agents.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Recommanded Product: 1214711-48-4. 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: (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, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about Carbene-Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products. Author is Liu, Yingguo; Majhi, Pankaj Kumar; Song, Runjiang; Mou, Chengli; Hao, Lin; Chai, Huifang; Jin, Zhichao; Chi, Yonggui Robin.

A catalytic dynamic kinetic resolution and asym. acylation reaction of hydroxyphthalides is developed [e.g., o-carboxybenzaldehyde (in equilibrium with hydroxyphthalide) + Me 4-formylbenzoate → I (96%, 98:2 e.r.) in presence of chiral NHC precatalyst]. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asym. modification of natural products and other functional mols. that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.

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Reference:
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: 1214711-48-4, is researched, SMILESS is 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, Molecular C18H13BCl3F4N3OJournal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called N-Heterocyclic Carbene Catalyzed Asymmetric Hydration: Direct Synthesis of α-Protio and α-Deuterio α-Chloro and α-Fluoro Carboxylic Acids, Author is Vora, Harit U.; Rovis, Tomislav, the main research direction is heterocyclic carbene catalyzed asym hydration chloro aldehyde halo enal; enantioselective synthesis chloro fluoro deuterio carboxylic acid.Formula: C18H13BCl3F4N3O.

Asym. hydration of α,α-dichloro aldehydes and α-halo enals via a NHC-catalyzed redox process to yield enantioenriched α-chloro and α-fluoro carboxylic acids is described herein. The developed reaction allows for installation of an α-deuterium to give rise to enantioenriched α-deutero α-halo acids using D2O as the deuteron source.

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Reference:
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 Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters, the main research direction is catalytic asym hydrogenation alpha dehydroamido boronate ester; alkyl amidoboronic ester preparation reaction; crystal mol structure cyclohexyl tetramethyldioxaborolanylethyl oxazolidinone.Quality Control of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

The direct catalytic asym. hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and 99% ee). The utility of the products has been demonstrated by transformation to their corresponding boronic acid derivatives by a Pd-catalyzed borylation reaction and an efficient synthesis of a potential intermediate of bortezomib. The clean, atom-economic and environment friendly nature of this catalytic asym. hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic esters of great potential in the area of organic synthesis and medicinal chem.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Liu, Xian; Wen, Jialin; Yao, Lin; Nie, Huifang; Jiang, Ru; Chen, Weiping; Zhang, Xumu published an article about the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8,SMILESS:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10 ).Product Details of 36620-11-8. 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:36620-11-8) through the article.

The highly chemo- and enantioselective hydrogenation of (E)-2-substituted-4-oxo-2-alkenoic acids was established for the first time using the Rh/JosiPhos complex, affording a series of chiral α-substituted-γ-keto acids with excellent results (up to 99% yield and >99% ee) and high efficiency (up to 3000 TON). In addition, the importance of this methodol. was further demonstrated by a concise and gram-scale synthesis of the anti-inflammatory drug (R)-flobufen.

After consulting a lot of data, we found that this compound(36620-11-8)Product Details of 36620-11-8 can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
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 A Computational Study of Asymmetric Hydrogenation of 2-Phenyl Acrylic Acids Catalyzed by a Rh(I) Catalyst with Ferrocenyl Chiral Bisphosphorus Ligand: The Role of Ion-Pair Interaction, the main research direction is phenyl acrylic acid rhodium catalyst asym hydrogenation mechanism.Synthetic Route of C14H8BF4Rh.

Asym. hydrogenation reaction is one of the most efficient synthetic methods to form useful chiral compounds for synthetic chem., medicinal chem. and material chem. Generally, the enantioselectivity of many hydrogenation reactions is controlled by steric hindrance between the chiral ligand and substrate. Recently, Zhang group developed a highly asym. hydrogenation of 2-aryl and 2-alkyl acrylic acids catalyzed by a Rh(I) catalyst with a chiral Wudaphos ligand. The excellent enantioselectivity of this asym. reaction was proposed to be controlled by ion-pair interaction between the substrate and chiral ligand. In this study, a systematic d. functional theory study has been carried out to investigate the reaction mechanism and origin of the enantioselectivity. Our computational results suggest that this reaction follows the classic mechanism involving oxidative addition of H2, migratory insertion and reductive elimination. Different from the C=C coordination to the metal in the common oxidative addition step, our study found that the chelation of the carboxyl group of the substrate to the cationic Rh(I) metal is more favorable in this oxidative addition step. The high enantioselectivity is proposed to be dictated by a better catalyst/substrate geometric complementarity in the major pathway to have less distortion of the catalyst for a strong ion-pair interaction.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Name: Bis(norbornadiene)rhodium (I) tetrafluoroborate. 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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about 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 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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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Gilbert, Sophie H.; Fuentes, Jose A.; Cordes, David B.; Slawin, Alexandra M. Z.; Clarke, Matthew L. published an article about the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8,SMILESS:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10 ).Application of 36620-11-8. 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:36620-11-8) through the article.

The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions These catalysts enable the use of lower amounts of aryl boronic acid in an asym. arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures

After consulting a lot of data, we found that this compound(36620-11-8)Application of 36620-11-8 can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider