Tag: 600-700

In 2017,Wen, Lu; Yue, Zhenting; Zhang, Haiyan; Chong, Qinglei; Meng, Fanke published 《Cu-Catalyzed Enantioselective Boron Addition to N-Heteroaryl-Substituted Alkenes》.Organic Letters published the findings.Product Details of 210169-54-3 The information in the text is summarized as follows:

Catalytic enantioselective Cu-B(pin) (pin = pinacolato) addition to N-heteroaryl-substituted alkenes followed by protonation promoted by phosphine-Cu complexes is presented. The resulting alkylboron products that contain a N-heteroaryl moiety are afforded in up to 97% yield and 99:1 enantiomeric ratio. The highly versatile C-B(pin) bond can be converted to a range of useful functional groups, delivering a variety of enantiomerically enriched building blocks that are otherwise difficult to access. The utility of this method is further demonstrated by application to a fragment synthesis of biol. active mol. U-75302. Preliminary mechanistic studies revealed that the adjacent N atom of the heterocycles plays a unique role in high reactivity and enantioselectivity. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes, stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydesProduct Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2022,Xu, Qi; Zhang, Huan; Ge, Fang-Bei; Wang, Xiao-Mei; Zhang, Peng; Lu, Chuan-Jun; Liu, Ren-Rong published an article in Organic Letters. The title of the article was 《Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers》.Product Details of 210169-54-3 The author mentioned the following in the article:

The copper(I) catalysis using a bis(phosphine) dioxide ligand could catalyze the desym. C-H arylation of prochiral bipyrroles was reported. More than 50 nitrogen-nitrogen atropisomers I [R1 = Ph, 3-ClC6H4, 2-naphthyl, etc.; R2 = Me, Et, Bn, etc.; R3 = Me, Et, i-Pr; R4 = H, Me; R1R4 = CH=CH-CH=CH; Ar = Ph, 4-MeC6H4, 3-ClC6H4, etc.] were achieved in good to excellent yields with excellent enantioselectivities (≤97% yield, ≤98% ee). The reaction proceeded under mild conditions with good functional group compatibility on arenes and diaryliodonium salts. Moreover, this principle enabled iterative arylation of the bipyrroles to enantioselectively arylate different positions during the catalysis of copper. In addition to this study using (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, there are many other studies that have used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3) was used in this study.

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

The author of 《Synthesis of N-aryl β-amino acid derivatives via Cu(II)-catalyzed asymmetric 1,4-reduction in air》 were Li, Min; Xia, Hong-Feng; Yang, Li-Yao; Hong, Tao; Xie, Lin-Jie; Li, Shijun; Wu, Jing. And the article was published in RSC Advances in 2019. Electric Literature of C38H28O4P2 The author mentioned the following in the article:

In the presence of the inexpensive and stable stoichiometric reductant polymethylhydrosiloxane (PMHS) as well as certain amounts of appropriate alc. and base additives, the non-precious metal copper-catalyzed asym. 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N-aryl β-enamino esters was well realized to afford a diverse range of N-aryl β-amino acid esters in high yields and excellent enantioselectivities (26 examples, 90-98% ee). This approach tolerated the handling of both catalyst and reactants in air without special precautions. The chiral products obtained were successfully converted to the corresponding enantiomerically enriched β-lactam and unprotected β-amino acid ester, which highlighted the synthetic utility of the developed catalytic procedure. In the experimental materials used by the author, we found (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Electric Literature of C38H28O4P2)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Electric Literature of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

The author of 《Enantioselective liquid-liquid extraction of DL-mandelic acid using chiral diphosphine ligands as extractants》 were Ma, Yu; Liu, Xiong; Zhou, Wenqi; Cao, Ting. And the article was published in Chirality in 2019. Related Products of 210169-54-3 The author mentioned the following in the article:

In order to expand the application range of chiral diphosphine ligands, (S)-BINAP, (S)-SEGPHOS, and (S)-MeO-BIPHEP were employed as extractants to recognize DL-mandelic acid. The results indicated that (S)-SEGPHOS-Cu exhibited considerable ability to recognize DL-mandelic acid with operational enantioselectivity (α) of 2.677. The process of extraction of DL-mandelic acid using (S)-SEGPHOS-Cu as extractant was systematically investigated. Performance factor (pf) was adopted to comprehensively evaluate the extraction After optimization by response surface methodol. (RSM), the optimal extraction condition is temperature of 5.5°C, (S)-SEGPHOS-Cu concentration of 3.0 mmol/L, and pH of 8.0. And the predicted and exptl. maximum values of pf were 0.26374 and 0.26839, resp. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Related Products of 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Related Products of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cruche, Corentin; Neiderer, William; Collins, Shawn K. published their research in ACS Catalysis in 2021. The article was titled 《Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences》.Category: chiral-phosphine-ligands The article contains the following contents:

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Category: chiral-phosphine-ligands)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Catalyst control over sixfold stereogenicity》 was written by Wu, Xingxing; Witzig, Reto M.; Beaud, Rodolphe; Fischer, Christian; Haussinger, Daniel; Sparr, Christof. Electric Literature of C38H28O4P2This research focused ontrialkenyl pyrroloanthracene rhodium catalyst regioselective enantioselective cycloaddition. The article conveys some information:

The sixfold stereogenicity by stereoselective catalysis was reported. By controlling a configurationally stable stereogenic axis with six large rotational barriers, a catalytic [2 + 2 + 2] cyclotrimerization selectively governed the formation of one of six stereoisomers with up to 0:0:2:98:0:0 stereocontrol. Moreover, the stereoselectivity was redirectable by stereodivergent catalysis, providing four of the six stereoisomers as major stereoisomers. The underpinnings of conformational anal. and stereoselective catalysis was thereby conceptually reunited. Novel mol. architectures featuring distinct chem. topologies and unexplored chem. designs were anticipated from catalyst control over higher-order stereogenicity. In the experimental materials used by the author, we found (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Electric Literature of C38H28O4P2)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Electric Literature of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2022,Yang, Ninglei; Dong, Ming; Tong, Xiaofeng published an article in Organic Letters. The title of the article was 《Pd(0)-Catalyzed Intramolecular Reductive Heck Reaction of Vinyl Iodide and Oxime Ether: Enantioselective Synthesis of Cyclic Allylic N-Alkoxy Amine》.Product Details of 210169-54-3 The author mentioned the following in the article:

Reported the Pd(0)-catalyzed intramol. reductive Heck reaction of vinyl iodide and oxime ether with the use of formic acid as the reductant. It was found that the TsOH additive plays a crucial role in the reaction efficiency and the (S)-SEGPhos ligand enables cyclic allylic N-alkoxy amine products with high enantioselectivity. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,ACS Catalysis included an article by Batuecas, Maria; Luo, Junfei; Gergelitsova, Ivana; Kramer, Katrina; Whitaker, Daniel; Vitorica-Yrezabal, Inigo J.; Larrosa, Igor. SDS of cas: 210169-54-3. The article was titled 《Catalytic Asymmetric C-H Arylation of (η6-Arene)Chromium Complexes: Facile Access to Planar-Chiral Phosphines》. The information in the text is summarized as follows:

A catalytic asym. direct C-H arylation of (η6-arene)chromium complexes to obtain planar-chiral compounds is reported. The use of the hemilabile ligand H8-BINAP(O) is key to providing high enantioselectivity in this transformation. We show that this methodol. opens the door to the synthesis of a variety of planar-chiral chromium derivatives which can be easily transformed into planar chiral mono- or diphosphines. Mechanistic studies, including synthesis and characterization of Pd and Ag complexes and their detection in the reaction mixture, suggest a Pd-catalyzed/Ag-promoted catalytic system where Ag carries out the C-H activation step. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3SDS of cas: 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.SDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2017,Mifleur, Alexis; Merel, Delphine S.; Mortreux, Andre; Suisse, Isabelle; Capet, Frederic; Trivelli, Xavier; Sauthier, Mathieu; Macgregor, Stuart A. published 《Deciphering the Mechanism of the Nickel-Catalyzed Hydroalkoxylation Reaction: A Combined Experimental and Computational Study》.ACS Catalysis published the findings.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

The [Ni(COD)2]/P∩P-catalyzed hydroalkoxylation of butadiene to form butenyl ethers is studied mechanistically, where P∩P = 1,4-bis(diphenylphosphino)butane (dppb) and 1,2-bis(diphenylphosphinomethyl)benzene (dppmb). Exptl. studies suggest the intermediacy of [(P∩P)Ni(0)(butadiene)] and [(P∩P)Ni(II)(allyl)] intermediates and rule out the involvement of Ni-H species. The related species [(dppb)Ni(1,4-diphenylbutadiene)], 1, and [(P∩P)Ni(crotyl)(Cl)] complexes 2 (P∩P = dppmb) and 3 (P∩P = dppb) have been synthesized and characterized on the basis of VT NMR spectroscopy and X-ray crystallog. studies. 2 And 3 are shown to be catalytically competent for the hydroalkoxylation reaction. Computational studies on [(dppmb)Ni(butadiene)] indicate a facile protonation that form a cationic allylic intermediate [(dppmb)Ni(η-C4H7)]OMe. C-O bond formation then occurs via external attack by the solvent-stabilized methoxide nucleophile. Hydroalkoxylation proceeds with modest computed barriers of ca. 15 kcal/mol and the butenyl ether product formation is only marginally exergonic, consistent with a reversible process operating under thermodn. control. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Computed Properties of C38H28O4P2In 2017 ,《Rh/SPO-WudaPhos-Catalyzed Asymmetric Hydrogenation of α-Substituted Ethenylphosphonic Acids via Noncovalent Ion-Pair Interaction》 was published in Organic Letters. The article was written by Yin, Xuguang; Chen, Caiyou; Li, Xiong; Dong, Xiu-Qin; Zhang, Xumu. The article contains the following contents:

Asym. hydrogenation of α-substituted ethenylphosphonic acids was successfully achieved by Rh/ferrocenyl chiral bisphosphorus ligand (SPO-Wudaphos) through noncovalent ion-pair interaction between the substrate and catalyst under mild reaction conditions without base. Chiral phosphonic acids were obtained with excellent results (up to 98% ee, >99% conversion, 2000 TON). Also, the control experiments showed that the noncovalent ion-pair interaction was critical in this asym. hydrogenation. In addition to this study using (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, there are many other studies that have used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Computed Properties of C38H28O4P2) was used in this study.

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis