Tag: 468.53

Palladium-catalyzed intramolecular direct arylation for phosphorus heterocycle synthesis was written by Chen, Yun-Rong;Duan, Wei-Liang. And the article was included in Synthesis in 2014.Synthetic Route of C33H25OP This article mentions the following:

A Pd-catalyzed intramol. direct arylation of bromo-substituted phosphine oxides is reported for the synthesis of P-containing heterocycles with good to excellent yields (78-98 %). E.g., reaction of Ph₂P(O)CH₂-2-C₆H₄Br with 10 mol% Pd(OAc)₂/10 mol% PPh₃ with K₂CO₃/DMA at 60° gave a 98% yield of 5,6-dihydro-5-phenylphosphanthridine 5-oxide. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Synthetic Route of C33H25OP).

(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. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Synthetic Route of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-Catalyzed Asymmetric Intramolecular Reductive Heck Desymmetrization of Cyclopentenes: Access to Chiral Bicyclo[3.2.1]octanes was written by Yuan, Zhenbo;Feng, Ziwen;Zeng, Yuye;Zhao, Xiaobin;Lin, Aijun;Yao, Hequan. And the article was included in Angewandte Chemie, International Edition in 2019.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine This article mentions the following:

A palladium-catalyzed asym. reductive Heck reaction of unactivated aliphatic alkenes, with eliminable β-hydrogen atoms, was realized for the first time. A series of optically active bicyclo[3.2.1]octanes bearing chiral quaternary and tertiary carbon stereocenters were obtained in good yields with excellent enantioselectivities, exhibited good functional-group tolerance and scalability. Moreover, deuterated optically active bicyclo[3.2.1]octanes were also obtained in high efficiency. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Safety 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. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

²H-quadrupolar coupling-based analysis of stereochemical and regiochemical memory in the Pd-catalyzed allylic alkylation of iso-cinnamyl type substrates employing the chiral monophosphine ligands “MOP” and “MAP” was written by Gouriou, Laure;Lloyd-Jones, Guy C.;Vyskocil, Stepan;Kocovsky, Pavel. And the article was included in Journal of Organometallic Chemistry in 2003.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine This article mentions the following:

The reaction of isocinnamyl acetate with NaC(Me)(CO₂Me)₂, catalyzed by Pd-MOP (MOP = 2-methoxy-2′-diphenylphosphino-1,1′-binaphthalene) is known to proceed with a regiochem. memory effect that results in the predominant generation of the branched alkylation product. The analogous reaction employing MAP as ligand (MAP = 2-N,N-dimethylamino-2′-diphenylphosphino-1,1′-binaphthalene) proceeds with normal regioselectivity to generate predominantly the linear isomer of product. A ²H-NMR based anal., employing quadrupolar coupling in a chiral liquid crystal matrix, has been developed to facilitate the simultaneous study of the regiochem. and stereochem. outcome of the reaction of both enantiomers of iso-cinnamyl ester substrates in ²H-labeled but racemic samples. The anal. allows the comparison of relative rates of two competing isomerization processes occurring in the π-allyl intermediates in the Pd-catalyzed reaction, one of which facilitates asym. induction, the other resulting in loss of regiochem. memory. It is demonstrated that the two processes are partially coupled and that this then limits the attainment of high global enantiomeric excess in the branched product to reactions that proceed with low regiochem. retention. A key factor for the observation of high regiochem. memory is found to be the nucleophilicity of the malonate anion and the electrophilicity of the Pd-π-allyl intermediate with reduction in the reactivity of either partner resulting in the onset of substantial loss of memory. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Safety 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Hidden Enantioselective Hydrogenation of N-Silyl Enamines and Silyl Enol Ethers in Net C:N and C:O Hydrosilylations Catalyzed by Ru-S Complexes with One Monodentate Chiral Phosphine Ligand was written by Baehr, Susanne;Oestreich, Martin. And the article was included in Organometallics in 2017.SDS of cas: 134484-36-9 This article mentions the following:

Ruthenium thiolate complexes with one chiral monodentate phosphine ligand are applied to enantioselective hydrosilylation of enolizable imines and ketones. The structural features of the catalyst exclude the presence of more than one phosphine ligand at the ruthenium center in the enantioselectivity-determining step. The enantiomeric excesses obtained in these reduction reactions are moderate (up to 66% ee), but the stereochem. outcome enables an exptl. anal. of the reaction pathways operative in this catalysis. A two-step sequence consisting of successive N-Si/O-Si dehydrogenative coupling and enamine/enol ether hydrogenation is the prevailing mechanism of action. Both steps involve cooperative bond activation at the Ru-S bond of the coordinatively unsaturated ruthenium complex: Si-H bond activation in the dehydrogenative coupling and heterolytic H-H splitting in the hydrogenation. Previously documented side reactions such as deprotonation/protonation equilibrium as well as competing direct C:N or C:O hydrogenation have been excluded. 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. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.SDS of cas: 134484-36-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis