Category: 221012-82-4

Quality Control of (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. 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: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Iridium-catalyzed asymmetric hydrogenation of pyridinium salts. Author is Ye, Zhi-Shi; Chen, Mu-Wang; Chen, Qing-An; Shi, Lei; Duan, Ying; Zhou, Yong-Gui.

A highly efficient iridium-catalyzed asym. hydrogenation of 2-substituted pyridinium salts is developed. A series of chiral 2-substituted piperidines were obtained in good to excellent yields and up to 93% ee.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | 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: 221012-82-4, is researched, SMILESS is COC(C=C1P(C2=CC=CC=C2)C3=CC=CC=C3)=NC(OC)=C1C4=C(OC)N=C(OC)C=C4P(C5=CC=CC=C5)C6=CC=CC=C6, Molecular C38H34N2O4P2Journal, Tetrahedron called First catalytic asymmetric hydrogenation of quinoxaline-2-carboxylates, Author is Maj, Anna M.; Heyte, Svetlana; Araque, Marcia; Dumeignil, Franck; Paul, Sebastien; Suisse, Isabelle; Agbossou-Niedercorn, Francine, the main research direction is iridium chiral ligand hydrogenation quinoxaline.Computed Properties of C38H34N2O4P2.

For the first time, the asym. hydrogenation of quinoxaline-2-carboxylates was performed successfully. The best catalysts are based on iridium complexes modified by chiral phosphorous ligands. Accelerated examination of ligands and catalysts has been undertaken by using a Chemspeed workstation (automated instrument) workstation enables carrying out, in parallel, eight independent catalytic reactions at the laboratory scale. Tetrahydroquinoxaline-2-carboxylates could be obtained with high yields and up to 74% ee. The synthesis of the target compounds was achieved using chiral ligands, such as (11aR)-10,11,12,13-tetrahydro-N,N-dimethyldiindeno[7,1-de:1′,7′-fg][1,3,2]dioxaphosphocin-5-amine [i/e/. (R)-siphos], 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-diphenylphosphine] [i.e., (S)-MeO-BIPHEP], (R)-Cl-MeO-BIPHEP, (R)-difluorphos, (R)-GARPHOS, (R)-P-PHOS, (S)-C3-TUNEPHOS [i.e., 1,1′-[(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[1,1-diphenylphosphine]], (S)-SEGPHOS, (S)-Xyl-SolPhos, CATASium T3, N-[(1R)-2-[(11bR)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yloxy]-1-methylethyl]-N’-phenylurea [i.e., ureaphos], SL-J404-1, SL-J006-1, SL-J002-1, SL-J003-1, SL-J009-1, SL-T002-1, SL-W006-1. Pre-catalysts included bis(acetato-κO,κO’)[(4R)-1,1′-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]]ruthenium [i.e., Ru(OAc)2[(R)-segphos]], [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium [i.e., RuCl[(R,R)-TsDPEN][p-cymene]] and [1,1′-(1S)-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]][4-cyano-3-nitrobenzenecarboxylato(2-)-κC6,κO1](η3-2-propen-1-yl)iridium.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine( cas:221012-82-4 ) is researched.Name: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine.Li, Zhanyu; Zhang, Mengru; Zhang, Yu; Liu, Shuang; Zhao, Jinbo; Zhang, Qian published the article 《Multicomponent Cyclopropane Synthesis Enabled by Cu-Catalyzed Cyclopropene Carbometalation with Organoboron Reagent: Enantioselective Modular Access to Polysubstituted 2-Arylcyclopropylamines》 about this compound( cas:221012-82-4 ) in Organic Letters. Keywords: enantioselective multicomponent synthesis arylcyclopropylamine; copper catalyzed cyclopropene carbometalation organoboron reagent. Let’s learn more about this compound (cas:221012-82-4).

The use of functional-group-tolerant organoboron in lieu of basic organometallic reagents in base-metal-catalyzed cyclopropene carbometalation opens three-component cyclopropane synthesis, as exemplified by the modular assembly of the highly medicinally relevant 2-arylcyclopropylamine (ACPA) framework via stereoselective carboamination. The highly enantioselective version has been realized to afford enantioenriched ACPAs with up to all three cyclopropyl carbons as stereogenic centers in one operation, representing the first example of enantioselective multicomponent cyclopropane synthesis. The reaction significantly improves the efficiency of ACPA synthesis and may inspire the development of other multicomponent cyclopropane syntheses beyond amination.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quality Control of (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Coumarins: Asymmetric Synthesis of (R)-Tolterodine. Author is Chen, Gang; Tokunaga, Norihito; Hayashi, Tamio.

Rhodium-catalyzed asym. 1,4-addition of arylboronic acids R1B(OH)2 (R1 = Ph, 4-MeC6H4, 3-MeC6H4, 4-ClC6H44, 4-MeOC6H4) to coumarins I (R = 6-Me, H, 6-MeO2C, 8-MeO) proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acac)(C2H4)2 and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones II in over 99% ee. This asym. reaction was applied to the synthesis of (R)-tolterodine.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Alame, Mohamad; Pestre, Nathalie; de Bellefon, Claude published the article 《Extensive re-investigations of pressure effects in rhodium-catalyzed asymmetric hydrogenations》. Keywords: pressure effect rhodium catalysis asym hydrogenation.They researched the compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine( cas:221012-82-4 ).HPLC of Formula: 221012-82-4. 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:221012-82-4) here.

The catalytic hydrogenation of three prochiral substrates Me Z-α-acetamidocinnamate (MAC), Me 2-acetamidoacrylate (M-Acrylate) and Et 4-methyl-3-acetamido-2-propanoate (E-EMAP) with rhodium precursors complexed with chiral diphosphines is reported at 1-30 bar hydrogen pressure. A library of 56 chiral diphosphines, including 23 BINAP derivatives, 7 JOSIPHOS, 5 BIPHEP, 3 DUPHOS derivatives, and 18 other ligands, was used. While it was generally accepted that high hydrogen pressure would result in lower ees, it is now demonstrated on a statistical basis that an equivalent distribution between beneficial and detrimental pressure effects on ee prevails and that the hydrogen pressure effect on enantioselectivity is not an isolated phenomenon since more than 33% of the reaction systems studied are strongly affected. In some case, the enantioselectivity can be improved up to 97% just by applying a higher hydrogen pressure. Extension of these conclusions to other non-chiral reagents is proposed.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine(SMILESS: COC(C=C1P(C2=CC=CC=C2)C3=CC=CC=C3)=NC(OC)=C1C4=C(OC)N=C(OC)C=C4P(C5=CC=CC=C5)C6=CC=CC=C6,cas:221012-82-4) is researched.Product Details of 13940-83-5. The article 《Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems》 in relation to this compound, is published in Tetrahedron: Asymmetry. Let’s take a look at the latest research on this compound (cas:221012-82-4).

The iridium complex-catalyzed asym. hydrogenation of quinolines in a poly(ethylene glycol) di-Me ether (DMPEG)/hexane biphasic system was studied. Catalysts with C2-sym. ligands such as Xyl-P-Phos, Cl-MeO-BIPHEP, SYNPHOS, and DifluorPhos are highly effective for this type of reaction. Most of the catalysts tested can be retained in DMPEG (Mn = 500), and the asym. hydrogenation of various quinoline substrates can be carried out in DMPEG/hexane biphasic system with up to 92% ee. The catalysts and the products can be separated via simple phase separation, and the reactivity/stereoselectivity of the catalysts can be retained for at least three reaction cycles.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | 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 Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon-Phosphorus Bonds by Nickel Catalysis, published in 2019-06-07, which mentions a compound: 221012-82-4, Name is (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, Molecular C38H34N2O4P2, HPLC of Formula: 221012-82-4.

The Ni-catalyzed cyclization of bisphosphine derivatives to form various phosphacycles is reported. The reaction proceeds via the cleavage of two C-P bonds of the bisphosphine. Unlike the previously reported Pd catalysts, the use of Ni as a catalyst allows for the cyclization that requires C(alkyl)-P bond cleavage. A phospha-nickelacycle intermediate was successfully isolated and characterized by x-ray crystallog.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

He, Cheng-Yu; Li, Qing-Hua; Wang, Xin; Wang, Feng; Tian, Ping; Lin, Guo-Qiang published an article about the compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine( cas:221012-82-4,SMILESS:COC(C=C1P(C2=CC=CC=C2)C3=CC=CC=C3)=NC(OC)=C1C4=C(OC)N=C(OC)C=C4P(C5=CC=CC=C5)C6=CC=CC=C6 ).Reference of (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. 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:221012-82-4) through the article.

Due to the low reactivity of 1,6-dienes and the challenge of selectively differentiating such two olefins, the development of metal-catalyzed asym. cyclization of 1,6-dienes remains largely underdeveloped. Herein, the authors describe the 1st Cu(I)-catalyzed asym. borylative cyclization of cyclohexadienone-tethered terminal alkenes (1,6-dienes) via a tandem process: the regioselective borocupration of the electron-rich terminal alkene and subsequent conjugate addition of stereospecific secondary alkyl-Cu(I) to the electron-deficient cyclohexadienone, affording enantioenriched bicyclic skeletons bearing three contiguous stereocenters in all cis-form. Meanwhile, this mild catalytic protocol is generally compatible with a wide range of functional groups, which allows further facile conversion of the cyclization products.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Related Products of 221012-82-4. 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: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Asymmetric amidocarbonylation of aldehyde and acetamide catalyzed by chiral palladium or rhodium complexes. Author is Xing, Ai-ping; Wang, Lai-lai; Kwok, Waihim.

The in situ prepared chiral catalyst of Pd/unchelating bidentate phosphine ligand L1 (DPPFF), bipyridine bidentate phosphine ligand L2 (P-PHOS), and bidentate phosphine ligand L3 ((S, Rp) -BPPF), and Rh/phosphite ligands L4-L6, have been applied in amidocarbonylation of cyclohexanecarboxaldehyde or phenylacetaldehyde. Pd/bipyridine bidentate phosphine ligand L2 gave the enantioselectivity 25% (S) and the yield 11% in amidocarbonylation of phenylacetaldehyde, When Pd/unchelating bidentate phosphine ligand L1 was employed in asym. amidocarbonylation of cyclohexanecarboxaldehyde, the enantioselectivity 4.3% (S) and the yield 15% were received.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Coumarins: Asymmetric Synthesis of (R)-Tolterodine, the main research direction is asym addition arylboronic acid coumarin rhodium catalyst; tolterodine asym synthesis rhodium catalyst addition arylboronic acid coumarin.Name: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine.

Rhodium-catalyzed asym. 1,4-addition of arylboronic acids R1B(OH)2 (R1 = Ph, 4-MeC6H4, 3-MeC6H4, 4-ClC6H44, 4-MeOC6H4) to coumarins I (R = 6-Me, H, 6-MeO2C, 8-MeO) proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acac)(C2H4)2 and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones II in over 99% ee. This asym. reaction was applied to the synthesis of (R)-tolterodine.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider