Category: chiral-phosphine-ligands

Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphineOn March 14, 2019, Wei, Xiao-Feng; Wakaki, Takayuki; Itoh, Taisuke; Li, Hong-Liang; Yoshimura, Takayoshi; Miyazaki, Aya; Oisaki, Kounosuke; Hatanaka, Miho; Shimizu, Yohei; Kanai, Motomu published an article in Chem. The article was 《Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes to Allenes》. The article mentions the following:

Here, a copper(I)-catalyzed enantioselective proton migration from skipped enynes to allenes I [R1 = Ph, 3-MeC6H4, 3-thienyl, etc.; R2 = H, Me, Bn, etc.] as an efficient approach in chiral allene synthesis was reported. With catalyst loading as low as 0.5 mol %, the reaction proceeded smoothly under mild conditions without the need for addnl. stoichiometric reagents or generation of waste. Novel chiral ligand containing diphenylphosphine moiety plays a critical role in furnishing high catalyst activity, promoting regioselective protonation to produce allenes instead of conjugated enynes and inducing axial chirality of allenes. The multiple roles of the chiral ligand were rationalized by d. functional theory calculations In the experimental materials used by the author, we found (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine)

(R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

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

Lou, Yan-Peng; Zheng, Chang-Wu; Pan, Ren-Ming; Jin, Qiao-Wen; Zhao, Gang; Li, Zhong published an article on February 6 ,2015. The article was titled 《Enantioselective Direct Mannich Reactions of Cyclic β-Ketoesters Catalyzed by Chiral Phosphine via a Novel Dual-Reagent Catalysis》, and you may find the article in Organic Letters.Formula: C18H24NP The information in the text is summarized as follows:

A combination of an amino acid derived chiral phosphine catalyst and Me acrylate efficiently catalyzed the direct Mannich reaction of cyclic β-ketoesters and N-Boc-aldimines. The dual-reagent catalysis was presumed to function through the formation of a zwitterion, which catalyzed the reaction with excellent stereocontrol via a hydrogen-bonding assisted chiral ion-pair pathway. After reading the article, we found that the author used (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Formula: C18H24NP)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Formula: C18H24NP This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

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

Electric Literature of C38H28O4P2In 2022 ,《Enantioselective [3+2] Cycloaddition of Vinylcyclopropanes with Alkenyl N-Heteroarenes Enabled by Palladium Catalysis》 appeared in Organic Letters. The author of the article were Chu, Wen-Dao; Wang, Ya-Ting; Liang, Tian-Tian; Long, Teng; Zuo, Jia-Yu; Shao, Zhihui; Chen, Bo; He, Cheng-Yu; Liu, Quan-Zhong. The article conveys some information:

Synthesis of (quinolinyl)-dioxaspiro[4.5]decane-6,10-diones such as I via catalytic enantioselective [3+2] cycloaddition reaction between vinyl cyclopropanes and alkenyl N-heteroarenes in the presence of LiBr and a Pd(0)/SEGPHOS complex was developed. Lithium bromide played a key role in improving the reactivity of alkenyl N-heteroarenes as a mild Lewis acid. In the experiment, the researchers used (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