Tag: 468.53

Suginome, Michinori et al. published their research in Journal of the American Chemical Society in 2003 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Computed Properties of C33H25OP

Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric Induction was written by Suginome, Michinori;Ohmura, Toshimichi;Miyake, Yoshihiro;Mitani, Shin’ichirou;Ito, Yoshihiko;Murakami, Masahiro. And the article was included in Journal of the American Chemical Society in 2003.Computed Properties of C33H25OP This article mentions the following:

Enantioenriched β-borylallylsilanes, e.g., (RO)2BC(:CH2)CH(SiMe2Ph)CH2CH2Ph [(RO)2B = 4,5-diorgano-1,3,2-dioxaborolanyl], were synthesized by Pd-catalyzed enantioface-selective addition of the Si-B bond of chiral 2-dimethylsilyl-4,5-diorgano-1,3,2-dioxaborolane (e.g., organo = Me, Ph, CO2Pri) to terminal allenes, CH2:C:CHCH2CH2Ph, using a Pd catalyst possessing a chiral monodentate phosphine ligand, e.g., CpPd(allyl)/PPh3. Use of a silylborane bearing a chiral auxiliary on the B atom was beneficial to gain enantioface selectivities ≤96% de. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Computed Properties of C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Computed Properties of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Yasui, Yoshizumi et al. published their research in Organic Letters in 2008 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Quality Control of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed Cyanoamidation was written by Yasui, Yoshizumi;Kamisaki, Haruhi;Takemoto, Yoshiji. And the article was included in Organic Letters in 2008.Quality Control of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine This article mentions the following:

The first enantioselective intramol. cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)2, optically active phosphoramidite I, and N,N-dimethylpropylene urea (DMPU) in decalin were found to be the best conditions. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Quality Control of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Quality Control of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Johansson, Magnus J. et al. published their research in Journal of the American Chemical Society in 2005 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Application In Synthesis of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Gold(I)-Catalyzed Stereoselective Olefin Cyclopropanation was written by Johansson, Magnus J.;Gorin, David J.;Staben, Steven T.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2005.Application In Synthesis of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine This article mentions the following:

A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinylcyclopropanes with high cis-selectivity. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Application In Synthesis of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Application In Synthesis of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Oi, S. et al. published their research in Journal of Molecular Catalysis A: Chemical in 1997 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Electric Literature of C33H25OP

Regioselective hydroesterification of styrene catalyzed by cationic palladium(II) complexes under mild conditions was written by Oi, S.;Nomura, M.;Aiko, T.;Inoue, Y.. And the article was included in Journal of Molecular Catalysis A: Chemical in 1997.Electric Literature of C33H25OP This article mentions the following:

The cationic palladium(II) complex [Pd(MeCN)2(PPh3)2](BF4)2 was found to be an active catalyst for hydroesterification (alkoxycarbonylation) of styrene using CO and methanol under very mild conditions. The system, Pd(OAc)2-PPh3–p-toluenesulfonic acid, which should give rise to a cationic species in situ, was also effective to produce the branched ester regioselectively in an excellent yield at ambient temperature Asym. hydroesterification of styrene by the use of chiral phosphines as ligands was also studied. The hydroesterification of 4-isobutylstyrene gave α-methyl-4-(2-methylpropyl)benzeneacetic acid Me ester (i.e., ibuprofen Me ester). Also prepared was (S)-6-methoxy-α-methyl-2-naphthaleneacetic acid Me ester. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Electric Literature of C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Electric Literature of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Kocovsky, Pavel et al. published their research in Journal of the American Chemical Society in 1999 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Formula: C33H25OP

Palladium(II) Complexes of 2-Dimethylamino-2′-diphenylphosphino-1,1′-binaphthyl (MAP) with Unique P,Cσ-Coordination and Their Catalytic Activity in Allylic Substitution, Hartwig-Buchwald Amination, and Suzuki Coupling was written by Kocovsky, Pavel;Vyskocil, Stepan;Cisarova, Ivana;Sejbal, Jan;Tislerova, Iva;Smrcina, Martin;Lloyd-Jones, Guy C.;Stephen, Susanna C.;Butts, Craig P.;Murray, Martin;Langer, Vratislav. And the article was included in Journal of the American Chemical Society in 1999.Formula: C33H25OP This article mentions the following:

Reaction of 2-dimethylamino-2′-diphenylphosphino-1,1′-binaphthyl with (PhCN)2PdCl2 gave an unusual Cσ-Pd bonding mode complex I. The catalytic activity in allylic substitution, Hartwig-Buchwald Amination, and Suzuki coupling of I is described. The crystal structure of I and two related complexes were described. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Formula: C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Formula: C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Batuecas, Maria et al. published their research in ACS Catalysis in 2019 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Formula: C33H25OP

Catalytic Asymmetric C-H Arylation of (η6-Arene)Chromium Complexes: Facile Access to Planar-Chiral Phosphines was written by Batuecas, Maria;Luo, Junfei;Gergelitsova, Ivana;Kramer, Katrina;Whitaker, Daniel;Vitorica-Yrezabal, Inigo J.;Larrosa, Igor. And the article was included in ACS Catalysis in 2019.Formula: C33H25OP This article mentions the following:

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 many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Formula: C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Formula: C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Lin, Zi-Qi et al. published their research in Angewandte Chemie, International Edition in 2015 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Reference of 134484-36-9

Palladium-Catalyzed Enantioselective C-H Arylation for the Synthesis of P-Stereogenic Compounds was written by Lin, Zi-Qi;Wang, Wei-Zhen;Yan, Shao-Bai;Duan, Wei-Liang. And the article was included in Angewandte Chemie, International Edition in 2015.Reference of 134484-36-9 This article mentions the following:

A palladium-catalyzed enantioselective C-H arylation of N-(o-bromoaryl)-diarylphosphinic amides is described for the synthesis of phosphorus compounds bearing a P-stereogenic center. The method provides good enantioselectivities and high yields. The products were readily transformed into P-chiral biphenyl monophosphine ligands. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Reference of 134484-36-9).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Reference of 134484-36-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Sakai, Masaaki et al. published their research in Angewandte Chemie, International Edition in 1998 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.SDS of cas: 134484-36-9

Rhodium-catalyzed addition of organoboronic acids to aldehydes was written by Sakai, Masaaki;Ueda, Masato;Miyaura, Norio. And the article was included in Angewandte Chemie, International Edition in 1998.SDS of cas: 134484-36-9 This article mentions the following:

The title reaction of RB(OH)2 (R = Ph, p-anisyl, o-, p-tolyl, p-FC6H4, 2,4,6-Me3C6H2, trans-BuCH:CH) with R1CHO (R1 = Ph, p-F3CC6H4, p-NCC6H4, p-AcC6H4, p-BrC6H4, p-tolyl, p-anisyl, 2-furyl, 1-naphthyl, C5H11, C6H11) in the presence of Rh(acac)(CO)2 in aqueous DME gave 31-97% 16 R1RCHOH. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9SDS of cas: 134484-36-9).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.SDS of cas: 134484-36-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Praz, Jezabel et al. published their research in Advanced Synthesis & Catalysis in 2012 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Electric Literature of C33H25OP

Evaluation of the Chiral DIANANE Backbone as Ligand for Organolithium Reagents was written by Praz, Jezabel;Guenee, Laure;Aziz, Sarwar;Berkessel, Albrecht;Alexakis, Alexandre. And the article was included in Advanced Synthesis & Catalysis in 2012.Electric Literature of C33H25OP This article mentions the following:

Novel endo,endo-2,5-diaminonorbonane-derived tertiary C2-sym. diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asym. deprotonation, asym. bromine-lithium exchange, and enantioselective addition of aryl- and alkylithium reagents to aromatic aldimines. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Electric Literature of C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Electric Literature of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wang, Qing et al. published their research in ACS Catalysis in 2022 | CAS: 134484-36-9

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Electric Literature of C33H25OP

Enantioselective Nickel-Catalyzed Si-C(sp2) Bond Activation and Migratory Insertion to Aldehydes: Reaction Scope and Mechanism was written by Wang, Qing;Zhong, Kang-Bao;Xu, Hao;Li, Shi-Nan;Zhu, Wei-Ke;Ye, Fei;Xu, Zheng;Lan, Yu;Xu, Li-Wen. And the article was included in ACS Catalysis in 2022.Electric Literature of C33H25OP This article mentions the following:

Transition-metal-catalyzed Si-C bond activation is one of the most important processes in both organosilicon chem. and homogeneous catalysis that is still rarely reported in the past decades, and the enantioselective versions based on transition-metal-catalyzed Si-C bond activation remain an ongoing challenge in asym. catalysis. Herein, the authors report a convenient and enantioselective Si-C bond cleavage-initiated [4 + 2] annulation of benzosilacyclobutenes with aldehydes, which provides an access to the direct synthesis of chiral six-membered oxasilacycles and their derivatives with high yields and enantioselectivities (up to 97% ee). The catalytic asym. reaction proceeds smoothly with the aid of a chiral TADDOL-derived phosphoramidite ligand and its chiral Ni complex with a suitable cavity. By switching the work-up of the reaction involved, the present strategy may be extended to subsequent downstream transformations of silyl ether-containing oxasilacycles to give chiral o-tolyl arylmethanols with high ees and quant. conversions. Exptl. results support that the strategy of Si-mediated organic synthesis controlled by Ni catalysis demonstrates a powerful potential for the facile synthesis of chiral alcs. and its drug-like derivatives Finally, mechanistic and computational studies of the Ni-catalyzed Si-C bond activation offer insights into the origin of the observed stereoselective outcome, and the d. functional theory calculation shows that the Ni-controlled Si-C(sp2) bond activation enables the controllable migratory insertion of benzaldehyde into the Ni-Si bond, which is recognized as the enantioselectivity-determining step. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Electric Literature of C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Electric Literature of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis