Category: 352655-61-9

Copper(I) Alkoxide-Catalyzed Alkynylation of Trifluoromethyl Ketones was written by Motoki, Rie;Kanai, Motomu;Shibasaki, Masakatsu. And the article was included in Organic Letters in 2007.Related Products of 352655-61-9 This article mentions the following:

A general method for direct alkynylation of trifluoromethyl ketones to afford the corresponding tertiary propargyl alcs., e.g., I, was developed using CuO^tBu-xantphos or phenanthroline complexes as catalysts. The ligands significantly enhanced the catalyst activity. In addition, KOTf, generated in the catalyst preparation step, exhibited some acceleration effects. A preliminary extension to a catalytic enantioselective CF₃-substituted tertiary propargyl alc. synthesis (up to 52% ee) is also described. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Related Products of 352655-61-9).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Related Products of 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ligand-Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins was written by Lu, Gang;Liu, Richard Y.;Yang, Yang;Fang, Cheng;Lambrecht, Daniel S.;Buchwald, Stephen L.;Liu, Peng. And the article was included in Journal of the American Chemical Society in 2017.Category: chiral-phosphine-ligands This article mentions the following:

The current understanding of ligand effects in transition metal catalysis is mostly based on the anal. of catalyst-substrate through-bond and through-space interactions, with the latter commonly considered to be repulsive in nature. The dispersion interaction between the ligand and the substrate, a ubiquitous type of attractive noncovalent interaction, is seldom accounted for in the context of transition-metal-catalyzed transformations. Herein we report a computational model to quant. analyze the effects of different types of catalyst-substrate interactions on reactivity. Using this model, we show that in the copper(I) hydride (CuH)-catalyzed hydroamination of unactivated olefins, the substantially enhanced reactivity of copper catalysts based on bulky bidentate phosphine ligands originates from the attractive ligand-substrate dispersion interaction. These computational findings are validated by kinetic studies across a range of hydroamination reactions using structurally diverse phosphine ligands, revealing the critical role of bulky P-aryl groups in facilitating this process. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Category: chiral-phosphine-ligands).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Enantioselective α-Allylation of Anilines Enabled by a Combined Palladium and Photoredox Catalytic System was written by Zhang, Hong-Hao;Zhao, Jia-Jia;Yu, Shouyun. And the article was included in ACS Catalysis in 2020.HPLC of Formula: 352655-61-9 This article mentions the following:

An enantioselective and branch-regioselective α-allylation of N-Me anilines with allylic acetates under dual palladium/photoredox catalysis was described. Readily available N-Me anilines were used as formal ”hard” alkyl nucleophiles without preactivation. Acetic acid was the only side product, which led to a high atom economy of this reaction. This protocol showed good functional group tolerance and broad scope. A range of chiral homoallylic amines I [R = Me, i-Pr, Ph, etc.; Ar¹ = Ph, 4-MeOC₆H₄, 4-NHAcC₆H₄, etc.; Ar² = Ph, 3-MeC₆H₄, 4-ClC₆H₄, etc.] were prepared in moderate to good yields (up to 76%) and excellent regioselectivities (B:L > 95:5 in all cases) and enantioselectivities (up to 96% ee) under mild reaction conditions. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9HPLC of Formula: 352655-61-9).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) 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. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.HPLC of Formula: 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cascade CuH-catalyzed conversion of alkynes into enantioenriched 1,1-disubstituted products was written by Gao, De-Wei;Gao, Yang;Shao, Huiling;Qiao, Tian-Zhang;Wang, Xin;Sanchez, Brittany B.;Chen, Jason S.;Liu, Peng;Engle, Keary M.. And the article was included in Nature Catalysis in 2020.HPLC of Formula: 352655-61-9 This article mentions the following:

Enantioenriched α-aminoboronic acids play a unique role in medicinal chem. and have emerged as privileged pharmacophores in proteasome inhibitors. Addnl., they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asym. alkene hydrofunctionalization has become a powerful tool to construct stereogenic C centers. By contrast, applying CuH cascade catalysis to achieve the reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, the authors report an efficient strategy to synthesize α-aminoboron compounds by a CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product rather than the alternative homodifunctionalized, 1,2-heterodifunctionalized or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9HPLC of Formula: 352655-61-9).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. HPLC of Formula: 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

A Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial, and Evaluation of Their Olfactory Activity was written by Beghetto, Valentina;Scrivanti, Alberto;Bertoldini, Matteo;Aversa, Manuela;Zancanaro, Aurora;Matteoli, Ugo. And the article was included in Synthesis in 2015.Computed Properties of C74H104O6P2 This article mentions the following:

Fragrances (S)-(+)-canthoxal, (R)-(-)-canthoxal [i.e., (S)-(+)-3-(4-methoxyphenyl)-2-methylpropanal, (R)-(-)-3-(4-methoxyphenyl)-2-methylpropanal] and (+)-Silvial and (-)-Silvial were synthesized in high enantiopurity by a simple four-step strategy starting from the com. available 4-substituted benzaldehydes. The key synthetic step is the catalytic asym. hydrogenation of the appropriate 3-aryl-2-(methyl)acrylic acid which has been carried out employing an in situ prepared ruthenium/axially chiral phosphine catalyst (up to 98% ee). The olfactory activity of the single enantiomers was evaluated. Under optimized conditions the synthesis of the target compounds was achieved using 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]phosphine] [i.e., (S)-3,5-di-tert-butyl-4-MeOBIPHEP] and bis(η⁶-benzene)di-μ-(chloro)dichlorodiruthenium as ligand-catalyst combination. The tilte compounds thus formed included (αS)-5-methoxyα-methylbenzenepropanal [i.e., (+)-(S)-canthoxal] and (αR)-5-methoxyα-methylbenzenepropanal [i.e., (-)-(R)-canthoxal]. Silvial enantiomers included (-)-α-methyl-4-(2-methylpropyl)benzenepropanal [i.e., (-)-Silvial] and (+)-α-methyl-4-(2-methylpropyl)benzenepropanal [i.e., (+)-Silvial]. Other catalysts included (1S,1′S)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-(dimethylamino)phenylmethyl]ferrocene [(RS)-MandyPhos], 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-diphenylphosphine [(S)-MeOBIPHEP], 1,1′-[(1R)-[1,1′-binaphthalene]-2,2′-diyl]bis[1,1-diphenylphosphine] [(R)-BINAP]. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Computed Properties of C74H104O6P2).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) 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. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Computed Properties of C74H104O6P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Toward Asymmetric Synthesis of Pentaorganosilicates was written by van der Boon, Leon J. P.;Fuku-en, Shin-ichi;Slootweg, J. Chris;Lammertsma, Koop;Ehlers, Andreas W.. And the article was included in Topics in Catalysis in 2018.Category: chiral-phosphine-ligands This article mentions the following:

Introducing chiral silicon centers was explored for the asym. Rh-catalyzed cyclization of dihydrosilanes to enantiomerically enriched spirosilanes as targets to enable access to enantiostable pentacoordinate silicates. The steric rigidity required in such systems demands the presence of two naphthyl or benzo[b]thiophene groups. The synthetic approach to the expanded spirosilanes extends Takai’s method (Kuninobu et al. in Angew Chem Int Ed 52(5):1520-1522, 2013) for the synthesis of spirosilabifluorenes in which both a Si-H and a C-H bond of a dihydrosilane are activated by a rhodium catalyst. The expanded dihydrosilanes were obtained from halogenated aromatic precursors. Their asym. cyclization to the spirosilanes were conducted with [Rh(cod)Cl]₂ in the presence of the chiral bidentate phosphine ligands (R)-BINAP, (R)-MeO-BIPHEP, and (R)-SEGPHOS, including derivatives with P-(3,5-t-Bu-4-MeO)-Ph (DTBM) groups. The highest enantiomeric excess of 84% was obtained for 11,11′-spirobi[benzo[b]-naphtho[2,1-d]silole] with the DTBM-SEGPHOS ligand. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Category: chiral-phosphine-ligands).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Catalytic Enantioselective Conjugate Alkynylation of α,β-Unsaturated 1,1,1-Trifluoromethyl Ketones with Terminal Alkynes was written by Sanz-Marco, Amparo;Blay, Gonzalo;Munoz, M. Carmen;Pedro, Jose R.. And the article was included in Chemistry – A European Journal in 2016.SDS of cas: 352655-61-9 This article mentions the following:

The first catalytic enantioselective conjugate alkynylation of α,β-unsaturated 1,1,1-trifluoromethyl ketones has been carried out. Terminal alkynes and 1,3-diynes were treated with trifluoromethyl ketones in the presence of a low catalytic load of a Cu^I-MeOBIPHEP complex (2.5 mol %) and triethylamine (10 mol %) to give the corresponding trifluoromethyl ketones bearing a propargylic stereogenic center at the β position with good yields and excellent enantiomeric excesses in most of the cases. No 1,2-addition products were formed under the reaction conditions. The procedure showed broad substrate scope for alkyne, diyne, and enone. A rationale for the observed stereochem. has been provided. Finally, the potential application of the reaction products in the synthesis of chiral tetrahydrofurans bearing a trifluoromethylated quaternary stereocenter has been devised. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9SDS of cas: 352655-61-9).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. SDS of cas: 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis