Tag: M.W=300-400

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 HMF and furfural: Promising platform molecules in rhodium-catalyzed carbonylation reactions for the synthesis of furfuryl esters and tertiary amides.Application of 36620-11-8.

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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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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

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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Reference:
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 Practical and efficient preparation of the chiral 4-bromotryptophan derivative by Rh-catalyzed hydrogenation, the main research direction is bromotryptophan enantioselective preparation rhodium catalyzed asym hydrogenation bromoindole.Product Details of 36620-11-8.

An efficient three-step sequence has been developed for the preparation of a chiral 4-bromotryptophan derivative starting from the com. available 4-bromoindole. Key to the synthesis was the generation of the chiral center via a Rh-catalyzed asym. hydrogenation of a dehydrotryptophan precursor with 95% yield and >99% ee. Notably, the whole synthetic route required no column chromatog. operations and was readily conducted on large scales.

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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: 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, Journal of Physical Chemistry C called 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., the main research direction is acetate pyruvate MRI contrast agent preparation sidearm parahydrogen hydrogenation.Electric Literature of C14H8BF4Rh.

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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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

SDS of cas: 36620-11-8. 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 Functionalized pyrroles from vinylaziridines and alkynes via rhodium-catalyzed domino ring-opening cyclization followed by C=C bond migration. Author is Wan, Shu-Hao; Liu, Shiuh-Tzung.

In the presence of Rh(nbd)2BF4 (nbd = norbornadiene), an aziridinylpropenoate I underwent cycloaddition reactions with aryl alkynes such as RCCH (R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-F3CC6H4, 4-MeCOC6H4, 4-EtO2CC6H4, 2,4,6-Me3C6H2, 1-naphthyl) followed by isomerization of the intermediates with DABCO to yield arylpyrrolepropanoates such as II (R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-F3CC6H4, 4-MeCOC6H4, 4-EtO2CC6H4, 2,4,6-Me3C6H2, 1-naphthyl). An aziridinylpropenone underwent analogous cycloaddition and isomerization reactions with phenylacetylene to yield a phenylpyrrolylpropanone.

There is still a lot of research devoted to this compound(SMILES：[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10)SDS of cas: 36620-11-8, and with the development of science, more effects of this compound(36620-11-8) can be discovered.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Review, Angewandte Chemie, International Edition called Stereoelectronic Effects in Ligand Design: Enantioselective Rhodium-Catalyzed Hydrogenation of Aliphatic Cyclic Tetrasubstituted Enamides and Concise Synthesis of (R)-Tofacitinib, Author is Li, Chengxi; Wan, Feng; Chen, Yuan; Peng, Henian; Tang, Wenjun; Yu, Shu; McWilliams, J. Christopher; Mustakis, Jason; Samp, Lacey; Maguire, Robert J., which mentions a compound: 36620-11-8, SMILESS is [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10, Molecular C14H8BF4Rh, Category: quinuclidine.

We herein report the development of a conformationally defined, electron-rich, C2-sym., P-chiral bisphosphorus ligand, ArcPhos, by taking advantage of stereoelectronic effects in ligand design. With the Rh-ArcPhos catalyst, excellent enantioselectivities and unprecedentedly high turnovers (TON up to 10,000) were achieved in the asym. hydrogenation of aliphatic carbocyclic and heterocyclic tetrasubstituted enamides, to generate a series of chiral cis-2-alkyl-substituted carbocyclic and heterocyclic amine derivatives in excellent enantiomeric ratios. This method also enabled an efficient and practical synthesis of the Janus kinase inhibitor (R)-tofacitinib.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

SDS of cas: 36620-11-8. 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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Highly chemo- and enantioselective Rh-catalyzed hydrogenation of β-sulfonyl-α,β-unsaturated ketones: Access to chiral γ-ketosulfones. Author is Liu, Gang; Yin, Congcong; Yang, Xuanliang; Li, Anqi; Wang, Minyan; Zhang, Xumu; Dong, Xiu-Qin.

Rh-catalyzed highly chemo- and enantioselective hydrogenation of β-sulfonyl-α,β-unsaturated ketones was first successfully developed. Remarkably, a variety of enantioenriched γ-ketosulfones were generated in good to high yields with excellent chemo/enantioselectivities (82-99% yields, >99:1 chemoselectivity, 88 to >99% ee). Moreover, the gram-scale asym. hydrogenation was carried out smoothly in 97% yield and 97% ee. Preliminary DFT computations furnished a reasonable explanation for the high chemoselectivity and enantioselectivity.

There is still a lot of research devoted to this compound(SMILES：[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10)SDS of cas: 36620-11-8, and with the development of science, more effects of this compound(36620-11-8) can be discovered.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation, published in 2019, which mentions a compound: 36620-11-8, mainly applied to dihydro benzothiophene dioxide enantioselective preparation; benzothiophene dioxide hydrogenation rhodium catalyst, Product Details of 36620-11-8.

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

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Kinetic Resolution of Racemic 3,4-Disubstituted 1,4,5,6-Tetrahydropyridine and 3,4-Disubstituted 1,4- Dihydropyridines via Rh-Catalyzed Asymmetric Hydrogenation, published in 2020-02-21, which mentions a compound: 36620-11-8, mainly applied to piperidine tetrahydropyridine preparation; tetrahydropyridine dihydropyridine asym hydrogenation rhodium catalyst, Safety of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

Kinetic resolution of racemic 3,4-disubstituted 1,4,5,6-tetrahydropyridines and 3,4-disubstituted 1,4-dihydropyridines was developed by Rh-catalyzed asym. hydrogenation, affording chiral 3,4-disubstituted piperidines and chiral 3,4-disubstituted 1,4,5,6-tetrahydropyridines with high selectivity factors (s = up to 1057). Remarkably, all four stereoisomers of 3,4-disubstituted piperidine can be easily prepared using this method. Furthermore, the synthetic utility of this methodol. was demonstrated by efficient synthesis of antidepressant drug (-)-paroxetine.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider