Month: April 2022

Product Details 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 Porous organic polymers as heterogeneous ligands for highly selective hydroacylation. Author is Jiang, Ya-Nan; Li, Ding-Chang; Yang, Ying; Zhan, Zhuang-Ping.

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

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, Chinese Journal of Chemistry called 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, the main research direction is phenyl acrylic acid rhodium catalyst asym hydrogenation mechanism.Application In Synthesis of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

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

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 Practical and efficient preparation of the chiral 4-bromotryptophan derivative by Rh-catalyzed hydrogenation, published in 2020-02-13, which mentions a compound: 36620-11-8, mainly applied to bromotryptophan enantioselective preparation rhodium catalyzed asym hydrogenation bromoindole, Formula: C14H8BF4Rh.

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

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 Oxyanion Steering and CH-π Interactions as Key Elements in an N-Heterocyclic Carbene-Catalyzed [4 + 2] Cycloaddition.Recommanded Product: 1214711-48-4.

The N-heterocyclic carbene catalyzed [4 + 2] cycloaddition has been shown to give γ,δ-unsaturated δ-lactones in excellent enantio- and diastereoselectivity. However, preliminary computational studies of the geometry of the intermediate enolate rendered ambiguous both the origins of selectivity and the reaction pathway. Here, we show that a concerted, but highly asynchronous, Diels-Alder reaction occurs rather than the stepwise Michael-type or Claisen-type pathways. In addition, two crucial interactions are identified that enable high selectivity: an oxyanion-steering mechanism and a CH-π interaction. The calculations accurately predict the enantioselectivity of a number of N-heterocyclic carbene catalysts in the hetero-Diels-Alder reaction.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Wang, Jiang; Lin, Xin; Shao, Pan-Lin; Song, Jingyuan; Wen, Jialin; Zhang, Xumu published the article 《Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols》. Keywords: vicinal amino alc preparation enantioselective; iminoketone hydrogenation rhodium catalyst.They researched the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ).Application 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.

This study presents an Rh/DuanPhos-catalyzed double asym. hydrogenation of α-iminoketones R1C(O)C(=NPMP)R2 (R1 = Ph, 1-naphthyl, 2-thienyl, etc.; R2 = Ph, 2-naphthyl, 2-thienyl, etc.) for accessing chiral vicinal amino alcs., (1R,2S)-R1C(OH)C(NHPMP)R2 which are privileged motifs in pharmaceuticals, agrochems., fine chems., chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodol. has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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 Highly Chemo- and Enantioselective Hydrogenation of 2-Substituted-4-oxo-2-alkenoic Acids.Safety of Bis(norbornadiene)rhodium (I) tetrafluoroborate.

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.

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Reference:
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.Product Details of 36620-11-8.Cai, Nengjian; Mi, Fen; Wu, Yanmei; Song, Hao; Liu, Xiao-Yu; Qin, Yong published the article 《Practical and efficient preparation of the chiral 4-bromotryptophan derivative by Rh-catalyzed hydrogenation》 about this compound( cas:36620-11-8 ) in Tetrahedron Letters. Keywords: bromotryptophan enantioselective preparation rhodium catalyzed asym hydrogenation bromoindole. Let’s learn more about this compound (cas: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

Quality Control of Bis(norbornadiene)rhodium (I) tetrafluoroborate. 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 Azine-N-oxides as effective controlling groups for Rh-catalyzed intermolecular alkyne hydroacylation. Author is Moseley, Daniel F.; Kalepu, Jagadeesh; Willis, Michael C..

Azine N-oxide substituted aldehydes are used as highly effective substrates with good reactivity for intermol. hydroacylation of alkynes. Employing a Rh(I)-catalyst, a mild and scalable aldehyde C-H activation, that permits the coupling with unactivated terminal alkynes was achieved in good yields and with high regioselectivities (up to >20 : 1 l:b). Both substrates can tolerate a broad variety of functional groups. The reaction can also be applied to diazine aldehydes that contain a free N-lone pair. Conversion of the hydroacylation products to the corresponding azine, through a one-pot hydroacylation/deoxygenation sequence was also demonstrated. A one-pot hydroacylation/cyclization, using N-Boc propargylamine, addnl. leads to the synthesis of a bidentate pyrrolyl ligand.

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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: (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 activation of cyclopropylcarbaldehydes for Mannich reaction and δ-lactam formation: remote enantioselectivity control and dynamic kinetic asymmetric transformation, the main research direction is multicyclic lactam stereospecific asym diastereoselective preparation dynamic kinetic transformation; cyclopropylcarbaldehyde asym Mannich NHC catalyzed.SDS of cas: 1214711-48-4.

An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes was disclosed for the first time to yield δ-lactam compounds such as I [R = C6H5, 2-FC6H4, 2-thienyl, etc.; R1 = Me, Et, 4-O2NBn, R2 = H, Cl, Me, etc.]. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound was afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asym. transformation (DYKAT) processes. Multiple chiral functional mols. could be afforded from the lactam products through simple protocols with retentions of the optical purities.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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 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: (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 Stereodivergent Synthesis of Chromanones and Flavanones via Intramolecular Benzoin Reaction. Author is Wen, Genfa; Su, Yingpeng; Zhang, Guoxiang; Lin, Qiqiao; Zhu, Yujin; Zhang, Qianqian; Fang, Xinqiang.

The strategy of stereodivergent reactions on racemic mixtures (stereodivergent RRM) was employed for the first time in intramol. benzoin reactions and led to the rapid access of chromanones/flavanones with two consecutive stereocenters. The easily separable stereoisomers of the products were obtained with moderate to excellent enantioselectivities in a single step. Catechol type additives proved crucial in achieving the desired diastereo- and enantioselectivities.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider