Day: March 31, 2022

Safety of Bis(norbornadiene)rhodium (I) tetrafluoroborate. 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 Diverse saturated heterocycles from a hydroacylation/conjugate addition cascade.

Rhodium-catalyzed hydroacylation using alkynes substituted with pendant nucleophiles, delivers linear α,β-unsaturated enone intermediates with excellent regioselectivity. These adducts are used to construct a broad range of diversely substituted, saturated O-, N- and S-heterocycles in a one-pot process. Judicious choice of cyclisation conditions enabled isolation of O-heterocycles with high levels of diastereoselectivity. A variety of derivatization reactions are also performed, generating functionalized hydroacylation products. This sequence serves as a general approach for the synthesis of fully saturated heterocycles.

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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 Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation, the main research direction is dihydro benzothiophene dioxide enantioselective preparation; benzothiophene dioxide hydrogenation rhodium catalyst.Safety 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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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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 Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis, published in 2020-06-19, which mentions a compound: 36620-11-8, Name is Bis(norbornadiene)rhodium (I) tetrafluoroborate, Molecular C14H8BF4Rh, HPLC of Formula: 36620-11-8.

Nonracemic bis(dinaphthodioxaphosphepinyl)diaza-crown ethers such as I and II were prepared as ligands for rhodium-catalyzed enantioselective hydrogenation reactions of enamidoesters and enamides and for rhodium-catalyzed regioselective and enantioselective carbonylation reactions of styrenes. The ligands showed distinct activities and enantioselectivities in rhodium-catalyzed asym. hydrogenation and hydroformylation reactions. In enantioselective hydrogenation reactions using Rh(norbornadiene)2BF4 as the metal catalyst, I and II yielded N-acetyl amino esters with opposite absolute configurations. In rhodium-catalyzed hydroformylation reactions in the presence of Rh(acac)(CO)2 and II, the addition of sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate reversed the enantioselectivity of hydroformylation and increased it significantly.

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Quinuclidine – Wikipedia,
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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, Organic Chemistry Frontiers called Kinetic resolution of 2,2-disubstituted-1,3-diketones via carbene catalysis, Author is Xu, Weici; Li, Yuanzhen; Liu, Rui; Yang, Shuang; Liu, Jian; Fang, Xinqiang, the main research direction is formylbenzyl diketone carbene catalyst enantioselective regioselective kinetic resolution; formylalkyl diketone carbene catalyst enantioselective regioselective kinetic resolution.Safety 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.

The successful organocatalytic kinetic resolution of 1,3-diketones with central quaternary stereocenters through the introduction of internal nucleophiles was reported. Two basic resolution modes were established, allowing access to a broad scope of enantioenriched 1,3-diketones with quaternary stereocenters, together with a large variety of tetralone derivatives with vicinal fully substituted carbon centers, and both of them were not easily available via currently known methods. The inherent principles between the different combinations of ketone groups and the resolution patterns were also disclosed. This work constituted a good complementary choice for the construction of 1,3-diketones with quaternary stereogenic centers and provided insightful information for further studies on diketone substrate-mediated intramol. annulations and kinetic resolutions

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Recommanded Product: 36620-11-8. 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 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..

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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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate(SMILESS: [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10,cas:36620-11-8) is researched.Application of 1663-45-2. The article 《Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds》 in relation to this compound, is published in Organic & Biomolecular Chemistry. Let’s take a look at the latest research on this compound (cas:36620-11-8).

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

Related Products of 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 Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.

Regiocontrol in the Rh-catalyzed boration of vinyl arenes is typically dominated by the presence of the conjugated aryl substituent. However, small differences in TADDOL-derived chiral monophosphite ligands can override this effect and direct Rh-catalyzed hydroboration of β-aryl and β-heteroaryl methylidenes by pinacolborane to selectively produce either chiral primary or tertiary borated products. The regiodivergent behavior is coupled with enantiodivergent addition of the borane. The nature of the TADDOL backbone substituents and that of the phosphite moiety function synergistically to direct the sense and extent of regioselectivity and enantioinduction. Twenty substrates undergo each reaction mode with regioselectivity values reaching >20:1 and enantiomer ratios reaching up to 98:2. A variety of subsequent transformations illustrate the potential utility of each product.

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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: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ) is researched.Formula: C14H8BF4Rh.Jiang, Ya-Nan; Li, Ding-Chang; Yang, Ying; Zhan, Zhuang-Ping published the article 《Porous organic polymers as heterogeneous ligands for highly selective hydroacylation》 about this compound( cas:36620-11-8 ) in Organic Chemistry Frontiers. Keywords: thiomethyl arylaldehyde alkyne rhodium catalyst hydroacylation; methylsulfanylarylpropenone preparation regioselective diastereoselective. Let’s learn more about this compound (cas:36620-11-8).

A porous organic polymer (POL-dppe) was synthesized and employed as a heterogeneous ligand for selective hydroacylation of alkynes. The polymer shows high linear selectivity and catalytic efficiency toward a broad range of alkynes and β-S substituted aldehydes. Owing to the confinement effect of the microporous structure, POL-dppe was far superior to the monomeric dppe ligand in controlling the selectivity of electron-deficient alkynes. The use of a porous organic polymer as a regioselective and efficient ligand in hydroacylation is reported for the first time.

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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 Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration, the main research direction is chiral secondary benzylic boronic ester preparation; stereoselective hydroboration regioselective allylic phosphonate rhodium catalyst.Reference of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

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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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, Chemical Science called Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation, Author is Liu, Gongyi; Zhang, Heng; Huang, Yi; Han, Zhengyu; Liu, Gang; Liu, Yuanhua; Dong, Xiu-Qin; Zhang, Xumu, 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, 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