Category: 329735-68-4

The author of 《Theoretical and experimental optimization of a new amino phosphite ligand library for asymmetric palladium-catalyzed allylic substitution》 were Magre, Marc; Biosca, Maria; Norrby, Per-Ola; Pamies, Oscar; Dieguez, Montserrat. And the article was published in ChemCatChem in 2015. Formula: C24H34O2 The author mentioned the following in the article:

A new library of modular amino phosphite ligands PhCH(OPO2Z)CHRNR1Me (Z = 1,1′-biphenyl-2,2-diyl, 1,1′-binaphthyl-2,2′-diyl; R = H, Me; R1 = Me, tBu, CMe2Ph) obtained in a few synthetic steps from enantiopure amino alcs. has been tested in asym. Pd-catalyzed allylic substitution of 1,3-diphenyl-2-propen-1-ol acetate and 2-cyclohexenol acetate. The modular ligand design is crucial to find highly selective catalysts for each substrate type using a wide range of C-, N-, and O-nucleophiles. A DFT study of the species responsible for the enantiocontrol was used to optimize the ligand structure. By selecting the ligand components, we were able to identify unprecedented catalytic systems that can create new chiral C-C, C-N, and C-O bonds in a variety of substrate types (hindered and unhindered) in high yields and enantioselectivities (ee values up to 99 %). Further studies on the Pd-π-allyl intermediates provided a deep understanding of the effect of ligand structure in the origin of enantioselectivity. Potential applications of the new Pd/amino phosphite catalysts were demonstrated by the practical synthesis of a range of chiral carbocycles by simple tandem reactions, with no loss of enantioselectivity. The experimental process involved the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Formula: C24H34O2)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Formula: C24H34O2 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Category: alcohols-buliding-blocksOn October 16, 2003 ,《Synthesis of New Chiral Monodentate Phosphite Ligands and Their Use in Catalytic Asymmetric Hydrogenationã€?was published in Organic Letters. The article was written by Hua, Zihao; Vassar, Victor C.; Ojima, Iwao. The article contains the following contents:

New monodentate phosphite ligands have been developed from axially chiral biphenols, which show excellent enantioselectivity in the Rh(I)-catalyzed hydrogenation of di-Me itaconate. The new chiral ligand system is suitable to create libraries and possesses fine-tuning capability. Ligands thus prepared included (+)-(11aS)-4,8-bis(1,1-dimethylethyl)-1,2,10,11-tetramethyl-6-phenoxydibenzo[d,f][1,3,2]dioxaphosphepin, (11aS)-1,2,10,11-tetramethyl-6-phenoxydibenzo[d,f][1,3,2]dioxaphosphepin, (+)-(11aS)-4,8-bis(1,1-dimethylethyl)-1,2,10,11-tetramethyl-6-[(2-naphthalenyl)oxy]dibenzo[d,f][1,3,2]dioxaphosphepin, (+)-(11aS)-4,8-bis(1,1-dimethylethyl)-1,2,10,11-tetramethyl-6-[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]dibenzo[d,f][1,3,2]dioxaphosphepin, etc. The results came from multiple reactions, including the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Category: alcohols-buliding-blocks)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gao, Jihui; Ni, Jie; Yu, Rongrong; Cheng, Gui-Juan; Fang, Xianjie published an article on January 15 ,2021. The article was titled 《Ni-Catalyzed Isomerization-Hydrocyanation Tandem Reactions: Access to Linear Nitriles from Aliphatic Internal Olefinsã€? and you may find the article in Organic Letters.Formula: C24H34O2 The information in the text is summarized as follows:

A highly regioselective nickel-based catalyst system for the isomerization/hydrocyanation of aliphatic internal olefins is described. This benign tandem reaction provides facile access to a wide variety of aliphatic nitriles in good yields with excellent regioselectivities. Thanks to Lewis acid-free conditions, the protocol features board functional groups tolerance, including secondary amine and unprotected alc. groups. In addition to this study using (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol, there are many other studies that have used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Formula: C24H34O2) was used in this study.

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Formula: C24H34O2 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Formula: C24H34O2On October 25, 2021 ,《Density Functional Theory-Inspired Design of Ir/P,S-Catalysts for Asymmetric Hydrogenation of Olefins》 was published in Organometallics. The article was written by Faiges, Jorge; Borras, Carlota; Pastor, Isidro M.; Pamies, Oscar; Besora, Maria; Dieguez, Montserrat. The article contains the following contents:

In silico-based optimization of Ir/P,S-catalysts for the asym. hydrogenation of unfunctionalized olefins using (E)-1-(but-2-en-2-yl)-4-methoxybenzene as a benchmark olefin has been carried out. DFT calculations revealed that the thioether group has a major role in directing the olefin coordination. This, together with the configuration of the biphenyl phosphite group, has an impact in maximizing the energy gap between the most stable transition states leading to opposite enantiomers. As a result, the optimized catalyst proved to be efficient in the hydrogenation of a range of alkenes with the same substitution pattern and olefin geometry as the benchmark olefin, regardless of the presence of functional groups with different coordination abilities (ee values up to 97%). Appealingly, further modifications at the thioether groups and at the biaryl phosphite moiety allowed the highly enantioselective hydrogenation of olefins with different substitution patterns (e.g., α,β-unsaturated lactones and lactams, 1,1′-disubstituted enol phosphinates, and cyclic β-enamides; ee values up to >99%).(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Formula: C24H34O2) was used in this study.

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Formula: C24H34O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diolOn October 28, 2002 ,《Electronic Differences between Coordinating Functionalities of Chiral Phosphine-Phosphites and Effects in Catalytic Enantioselective Hydrogenation》 was published in Organometallics. The article was written by Suarez, Andres; Mendez-Rojas, Miguel A.; Pizzano, Antonio. The article contains the following contents:

A convenient synthesis of new chiral phosphine-phosphites (P-OP) was described. The versatility of the synthetic protocol developed gave ligands with different phosphine fragments and the choice of the stereogenic element location. Analyses of the values of 1JPSe of the corresponding diselenides are in accord with the expected lower σ-donor ability of the phosphite fragment, with respect to the phosphine group, and with an increase of phosphine basicity after substitution of Ph substituents by Me groups. Inspection of υ(CO) values on complexes RhCl(CO)(P-OP) demonstrated a variable π-acceptor ability of the phosphite group, compensating for the change of basicity of the phosphine functionality, as well as having a rather reduced electron d. at the metal center compared with diphosphine analogs. The distinct nature of the P functionalities also was evidenced in Rh-catalyzed enantioselective hydrogenation of Me Z-α-acetamidocinnamate (MAC). Thus, the coordination mode of the substrate is governed by the chiral ligand, directing the olefinic bond to a cis position with respect to the phosphite group, as demonstrated by NMR studies performed with [Rh(P-OP)(MAC)]+ complexes. In consequence, the phosphite group has a greater impact on the enantioselectivity of the product. However, the optical purity of the process also depends on the nature of the phosphine group, and hence, an appropriate election of both P functionalities is required for the attainment of excellent enantioselectivities (99% ee). After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Fuentes, Jose A.; Janka, Mesfin E.; Rodgers, Jody; Fontenot, Kevin J.; Buhl, Michael; Slawin, Alexandra M. Z.; Clarke, Matthew L. published their research in Organometallics on December 13 ,2021. The article was titled 《Effect of Ligand Backbone on the Selectivity and Stability of Rhodium Hydroformylation Catalysts Derived from Phospholane-Phosphites》.Recommanded Product: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The article contains the following contents:

A study on how ligand backbone structure has an impact on selectivity, rate, and catalyst stability of hydroformylation catalysts was prompted by some longer-term stability issues being discovered for a phospholane-phosphite with a [-CH2O-] backbone. Phospholane-phosphite ligands were synthesized. Catalysts made in situ from these ligands and [Rh(acac)(CO)2] gave iso-butanal selectivities up to 75% at 75-105°: the latter being a benchmark for iso-selectivity in reactions conducted at industrially meaningful temperatures A racemic Rh complex of a bidentate phospholane-phosphite from a tropos-biphenol with an extended backbone showed unusually high stability at high temperatures, combined with even better iso-selectivity in propene hydroformylation relative to the original complex. A related ligand with an electron-withdrawing group maintained the unusually high stability and improved activity. Characterization of the precatalysts [RhH(CO)2(L)] was accomplished using in situ HPIR spectroscopy and backed up by d. functional theory calculations (B3PW91-D3 level) and by NMR studies; the latter showed that the variation of the backbone also had a pronounced impact on the precatalyst structure. A key finding is that it is now possible to prepare phospholane-phosphite ligands that deliver high iso-butanal selectivity and that show no signs of degradation after several days even above typical reaction temperatures In one stability test, several kilograms of aldehydes were produced with TOF and selectivity being consistent over several days. In the experiment, the researchers used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Recommanded Product: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Recommanded Product: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diolOn September 25, 2006 ,《Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination》 was published in Organometallics. The article was written by Watson, Donald A.; Chiu, Melanie; Bergman, Robert G.. The article contains the following contents:

In situ combination of diphosphinic amides and Zr(NMe2)4 gave chiral Zr bis(amido) complexes. The complexes are competent catalysts for intramol. asym. alkene hydroamination, providing piperidines and pyrrolidines in up to 80% ee and high yield. This system uses an inexpensive precatalyst, readily prepared ligands and is the 1st asym. alkene hydroamination catalyst based upon a neutral Zr bis(amido) complex. In the experiment, the researchers used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diolOn October 23, 2017 ,《Molybdenum-Catalyzed Enantioselective Synthesis of Planar-Chiral (η5-Phosphacyclopentadienyl)manganese(I) Complexes and Application in Asymmetric Catalysis》 was published in Organometallics. The article was written by Ogasawara, Masamichi; Tseng, Ya-Yi; Uryu, Mizuho; Ohya, Naoki; Chang, Ninghui; Ishimoto, Hiroto; Arae, Sachie; Takahashi, Tamotsu; Kamikawa, Ken. The article contains the following contents:

Enantioselective desymmetrization of Cs-sym. (η5-2,5-dialkenylphospholyl)(allyldiphenylphosphine)manganese(I) dicarbonyl complexes 1 was realized by Mo-catalyzed asym. ring-closing metathesis (ARCM), and the corresponding bridged planar-chiral phosphacymantrene derivatives 2 were obtained in good yields with excellent enantioselectivity. The enantioselectivity of the ARCM reaction was strongly influenced by the structures of the phospholyl-bound alkenyl groups, and the highest enantioselectivity of up to 99% ee was achieved in the reaction of 1d,e, which possess the 2-methylpropenyl substituents at the 2- and 5-positions of the η5-phospholides. Single-enantiomeric planar-chiral 2d, which was obtained by the recrystallization of the highly enantiomerically enriched ARCM product, can serve as a chiral ligand for the Pd-catalyzed asym. allylic alkylation to show good enantioselectivity in up to 74% ee. The experimental part of the paper was very detailed, including the reaction process of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Name: (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2011,Chemistry – An Asian Journal included an article by Shi, Ce; Chien, Chih-Wei; Ojima, Iwao. Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol. The article was titled 《Synthesis of Chiral Biphenol-Based Diphosphonite Ligands and their Application in Palladium-Catalyzed Intermolecular Asymmetric Allylic Amination Reactions》. The information in the text is summarized as follows:

A library of new 2,2′-bis(diphenylphosphinoyloxy)-1,1′-binaphthyl (binapo)-type chiral diphosphonite ligands was designed and synthesized based on chiral 3,3′,5,5′,6,6′-hexasubstituted biphenols. These bop ligands have exhibited excellent efficiency in a palladium-catalyzed intermol. allylic amination reaction, which provides a key intermediate for the total synthesis of Strychnos indole alkaloids with enantiopurities of up to 96 % ee. In addition to this study using (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol, there are many other studies that have used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol) was used in this study.

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《(S)-2-[(N-arylamino)methyl]pyrrolidines-Based Phosphoramidite P,N-Ligand Library for Asymmetric Metal-Catalyzed Allylic Substitution and Conjugate 1,4-Addition》 was published in ChemistrySelect in 2016. These research results belong to Gavrilov, Konstantin N.; Mikhel, Igor S.; Chuchelkin, Ilya V.; Zheglov, Sergey V.; Gavrilov, Vladislav K.; Birin, Kirill P.; Tafeenko, Victor A.; Chernyshev, Vladimir V.; Goulioukina, Nataliya S.; Beletskaya, Irina P.. SDS of cas: 329735-68-4 The article mentions the following:

A library of easy-to-prepare and modular chiral P,N-phosphoramidites based on [1,1′-biaryl]-2,2′-diols and C1-sym. 1,2-diamines was designed and developed. The structures of the novel ligands were elucidated by 2-dimensional-NMR and confirmed in the solid state by x-ray diffraction anal. Stereoselectors of this type exhibited high enantioselectivities in Pd-catalyzed allylic substitution reactions of (E)-1,3-diphenylallyl acetate with NaSO2-p-Tol (up to 91% ee), CH2(CO2Me)2 (up to 89% ee), Pr2NH (up to 94% ee) and (EtO)2P(O)CH2NH2 as a novel nucleophile (up to 98% ee). Ee values of up to 88% and 72% were obtained in the Pd-catalyzed desymmetrization of N,N’-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate and in the Cu-catalyzed 1,4-conjugate addition of diethylzinc to chalcone, resp. The reactions of P,N-bidentate ligands with [Pd(Cod)Cl2] at molar ratios of L/M = 1 and 2 were studied using 1H, 13C, 13C-1H HSQC, 13C-1H HMBC, 1H-1H COSY, 1H-1H ROESY, DOSY and 31P NMR spectroscopy as well as HR ESI mass spectrometry. The results came from multiple reactions, including the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4SDS of cas: 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.SDS of cas: 329735-68-4 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts