Day: April 1, 2022

Related Products of 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 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. Author is Fan, Xiangru; Zheng, Lini; Yang, Yuhong; Dong, Xiu-Qin; Zhang, Xumu; Chung, Lung Wa.

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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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 N-Heterocyclic carbene catalyzed aza-benzoin reaction for access to α-aminoketone molecules containing benzothiazole fragments, published in 2021-08-13, which mentions a compound: 1214711-48-4, mainly applied to benzothiazole aminoketone preparation carbene catalyzed azabenzoincarboxaldehyde sulfonylimine, Synthetic Route of C18H13BCl3F4N3O.

An N-Heterocyclic carbene (NHC) catalyzed aza-benzoin reaction of benzothiazole-2-carboxaldehydes and N-sulfonylimines is reported for the first time. The target benzothiazole-containing aminoketone products bearing different substituents and substitution patterns can be obtained in good to excellent yields under mild conditions.

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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 Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation.SDS of cas: 36620-11-8.

Rh/ZhaoPhos-catalyzed asym. hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates I (R = H, Cl, F, MeO; R1 = CO2Me, CO2Et, CO2iPr) was successfully developed to prepare various chiral 4-substituted chromanes II with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5000) and the hydrogenation product II (R = H, R1 = CO2Et) was easily converted to access other important compounds, II (R = H, R1 = CO2H, CH2OH) which demonstrated the synthetic utility of this asym. catalytic methodol.

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Quinuclidine – Wikipedia,
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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: (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 Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis.Electric Literature of C18H13BCl3F4N3O.

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,
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HPLC of Formula: 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 Diverse saturated heterocycles from a hydroacylation/conjugate addition cascade. Author is Iwumene, Ndidi U. N.; Moseley, Daniel. F.; Pullin, Robert D. C.; Willis, Michael C..

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,
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Zhong, Yong-Li; Moore, Jeffrey C.; Shevlin, Michael; Shultz, C. Scott; Kosjek, Birgit; Chen, Yonggang; Janey, Jacob M.; Tan, Lushi published the article 《Scalable Asymmetric Synthesis of MK-8998, a T-type Calcium Channel Antagonist》. Keywords: scalable MK 8998 preparation enantioselective calcium channel antagonist.They researched the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ).Related Products of 36620-11-8. 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.

Two scalable and efficient synthetic routes for the synthesis of a T-type calcium channel antagonist MK-8998 were developed from a simple pyridine building block. The key step to set the stereochem. relied on either chiral rhodium catalyst-mediated asym. hydrogenation of an enamide or transamination of an arylketone that provided the corresponding product in high enantioselectivity and high yield.

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Quinuclidine – Wikipedia,
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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 Functionalized pyrroles from vinylaziridines and alkynes via rhodium-catalyzed domino ring-opening cyclization followed by C=C bond migration, the main research direction is pyrrolepropanoate pyrrolepropanone preparation; rhodium catalyst cycloaddition aryl alkyne aziridinylpropenoate isomerization DABCO.Electric Literature of C14H8BF4Rh.

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.

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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 Functionalized pyrroles from vinylaziridines and alkynes via rhodium-catalyzed domino ring-opening cyclization followed by C=C bond migration, the main research direction is pyrrolepropanoate pyrrolepropanone preparation; rhodium catalyst cycloaddition aryl alkyne aziridinylpropenoate isomerization DABCO.Name: Bis(norbornadiene)rhodium (I) tetrafluoroborate.

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.

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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, 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., the main research direction is carbocyclic heterocyclic amine enantioselective synthesis ligand catalyzed hydrogenation enamide; Tofacitinib enantioselective synthesis Rhodium bisphosphorus ligand catalyzed hydrogenation enamide; P ligands; asymmetric hydrogenation; enamides; stereoelectronic effects; tofacitinib.Formula: C14H8BF4Rh.

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

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 Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration, published in 2019, which mentions a compound: 36620-11-8, mainly applied to chiral secondary benzylic boronic ester preparation; stereoselective hydroboration regioselective allylic phosphonate rhodium catalyst, SDS of cas: 36620-11-8.

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,
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